[ CAS No. 147127-20-6 ] {[proInfo.proName]}

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Quality Control of [ 147127-20-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 147127-20-6 ]

SDS Specification

Alternatived Products of [ 147127-20-6 ]

Product Details of [ 147127-20-6 ]

CAS No. :	147127-20-6	MDL No. :	MFCD00943794
Formula :	C₉H₁₄N₅O₄P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SGOIRFVFHAKUTI-ZCFIWIBFSA-N
M.W :	287.21	Pubchem ID :	464205
Synonyms :	GS 1278;PMPA;TDF;(R)-PMPA;GS-1275	Chemical Name :	(R)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid

Calculated chemistry of [ 147127-20-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.44
Num. rotatable bonds :	5
Num. H-bond acceptors :	7.0
Num. H-bond donors :	3.0
Molar Refractivity :	67.48
TPSA :	146.19 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.41
Log Po/w (XLOGP3) :	-1.6
Log Po/w (WLOGP) :	-0.04
Log Po/w (MLOGP) :	-2.3
Log Po/w (SILICOS-IT) :	-1.93
Consensus Log Po/w :	-1.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.63
Solubility :	66.8 mg/ml ; 0.233 mol/l
Class :	Very soluble
Log S (Ali) :	-0.96
Solubility :	31.4 mg/ml ; 0.109 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.83
Solubility :	42.4 mg/ml ; 0.148 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.39

Safety of [ 147127-20-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P301+P310+P330-P405-P501	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 147127-20-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 147127-20-6 ]
Downstream synthetic route of [ 147127-20-6 ]

[ 147127-20-6 ] Synthesis Path-Upstream 1~2

1
[ 147127-20-6 ]
[ 379270-37-8 ]

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 4-7, p. 621 - 628
[2] Patent: US2013/90473, 2013, A1,
[3] Patent: US2013/90473, 2013, A1,
[4] Patent: US2016/115186, 2016, A1,
[5] Patent: US2017/56423, 2017, A1,
[6] Patent: WO2017/221189, 2017, A1,
[7] Patent: WO2017/221189, 2017, A1,
[8] Patent: CN108409790, 2018, A,
[9] Patent: CN108409788, 2018, A,

2
[ 147127-20-6 ]
[ 108-95-2 ]
[ 379270-37-8 ]
[ 383365-04-6 ]

Reference： [1] Patent: CN106478725, 2017, A,

[ 147127-20-6 ] Synthesis Path-Downstream 1~5

1
[ 3167-63-3 ]
[ 14047-28-0 ]
[ 147127-20-6 ]

Yield	Reaction Conditions	Operation in experiment
0.7 g		Example: 12 Preparation of 9-[2-(R)-(phosphonomethoxy)propyl] adenine (II) Method-B Magnesium di-tert-butoxide (1 .76 g) was added in four divided batches to a stirred suspension of 9-[2-(R)-(hydroxyl)propyl)adenine] (1 g) in N, N- dimethylformamide (3 ml) at 60-70C over a period of 1 h. The reaction mixture was heated to 90C and <strong>[3167-63-3]diethyl chloromethylphosphonate</strong> (1 .93 g) was added drop by drop to the reaction mixture over a period of 4 h. The reaction mixture was maintained at this temperature until the reaction was complete, as indicated by TLC. Nu, Nu-Dimethylformamide was distilled out under vacuum at 90-100C. To the residue thus obtained, aqueous hydrobromic acid (48% w/w, 10 ml) was added and the reaction mixture was heated to gentle reflux. After approximately 20 h at this condition, the reaction mixture was allowed to cool down to room temperature and filtered. The filtered solid was washed with dichloromethane (10 ml). The washing was concentrated to furnish a residue. The residue was combined with the filtrate and the combined filtrate was washed with dichloromethane (2 X 10 ml). To the aqueous layer, an aqueous solution of sodium hydroxide (50%) was added until the pH attained 2.1 -3. After several hours at room temperature, the aqueous layer was cooled to 0-5 C and stirred at this temperature for further hours to maximize precipitation of the desired product from the solution. The precipitated solid was filtered, washed with cold water (1 X 5 ml), acetone (2 X 5 ml) and dried to obtain 9-[2-(R)-(phosphonomethoxy)propyl]adenine; yield: 0.7 g.

Reference： [1]Patent: WO2016/178162,2016,A1 .Location in patent: Page/Page column 24-25

2
[ 23377-40-4 ]
D-alanine isopropyl ester hydrochloride [ No CAS ]
[ 147127-20-6 ]
(((((R)-1-(6-amino-9H-purin 9-yl)propan-2-yl)oxy)methyl)(3-(hexadecyloxy)propoxy)phosphoryl)-D-alanine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		PMPA (202 mg, 0.76 mmol) was added to the dried reaction flask,D-alanine isopropyl ester hydrochloride (230 mg, 1.38 mmol),Hexadecyloxypropanol (685 mg, 2.28 mmol) andAnhydrous pyridine (2 ml),Under nitrogen protection,Triethylamine (1.3 ml, 9.2 mmol) was added dropwise to the reaction solution,The mixture was reacted at 50 C for 10 minutes,Triphenylphosphine (1.4 g, 5.35 mmol) was added,Dithiopyridine (1.18 g, 5.35 mmol)In pyridine (3 ml)The reaction mixture was reacted overnight at 80 C.The residue was concentrated by column chromatography on silica gel (eluted with 0-20% ethyl acetate / petroleum ether followed by 0-8% methanol in dichloromethaneElution),The target compound V-17-a (161 mg, yield 31%) was obtained

Reference： [1]Patent: CN106565785,2017,A .Location in patent: Paragraph 0068

3
[ 23377-40-4 ]
[ 147127-20-6 ]
(((((R)-1-(6-amino-9H-purin 9-yl)propan-2-yl)oxy)methyl)(3-(hexadecyloxy)propoxy)phosphoryl)-D-alanine fumarate [ No CAS ]

Reference： [1]Patent: CN106565785,2017,A

4
[ 93765-68-5 ]
[ 147127-20-6 ]
C₂₁H₃₂N₇O₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 72.0h;	Anhydrous PMPA (0.3 g, 1 mmol) and DIEA (1 mL, 6 mmol) were placed in anhydrous DMF (2 mL). Chloromethyl morpholinocarbamate (3 mmol) was then added and then the suspension was stirred at room temperature for 3 days. The reaction was partitioned between CH 2 Cl 2 / isopropanol and 0.1 M citrate buffer (pH 6). The CH 2 Cl 2 layer was washed with water, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was taken up in methylene chloride and applied to a silica gel column (5 g, SiO 2). This was eluted with 25 mL of isopropanol in 0, 3, 6, 9, 12, 15, 18% (v / v) methylene chloride and then 21%, 100 mL of isopropanol in methylene chloride. Appropriate fractions were pooled and evaporated to give the desired product.

Reference： [1]Patent: JP2015/164934,2015,A .Location in patent: Paragraph 0201-0203

5
[ 23377-40-4 ]
[ 39825-33-7 ]
[ 147127-20-6 ]
9-[(R)-2-[[[[(S)-1-(isopropoxycarbonyl)ethyl]amino][(3-hexadecyloxy-1-propyl)oxy]phosphinyl]methoxy]propyl]adenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
628 g		L-alanine isopropyl ester hydrochloride 500gAnd potassium bicarbonate 730gIt was stirred at room temperature for 12 hours in DCM (2 kg).The mixture was then filtered and further rinsed with DCM (1 kg). The filtrate was dried on a molecular sieve bed until the water content of the solution was < 0.03%.The obtained L-alanine isopropyl ester was cooled to a pot temperature of -20 C for use.Weigh 500g of tenofovir (dried at 105 C in an oven for 3 hours before feeding) into a 2000ml flask, then add 1500g of thionyl chloride, heat to 55 C, after 10 minutes, continue to warm to 70 C and stir After 3 hours, pour into a 20 L rotary flask and distill the thionyl chloride under reduced pressure.After the end of the distillation, 7 kg of acetonitrile was added and refluxed at 85 C for 0.5 h.Add 630 g of <strong>[23377-40-4]3-hexadecyloxy-1-propanol</strong> in 10 portions (add once every 10 minutes).After the addition, the stirring was continued for 0.5 h under reflux.After slowly cooling to 35 C, then add 3 kg of dichloromethane,After further stirring for 0.5 h, 458 g of L-alanine isopropyl ester was added dropwise within 0.5 h.After stirring for 0.5 h, 350 g of triethylamine was added dropwise.After stirring for 0.5 h, the system was cooled to room temperature, suction filtered, and the filtrate was evaporated to dryness to ethyl acetate.The filter cake was stirred with 1 kg of ethyl acetate for 1 hour, and then filtered with suction. The filtrate was combined with the above steps. The combined ethyl acetate solution was washed twice with 6 kg of 5% aqueous potassium hydrogencarbonate solution and twice with 6 kg of 20% aqueous sodium chloride solution. The ethyl acetate solution was cooled to -7 C. After 2 h, suction filtration was started and the filtrate was evaporated to dryness. After evaporation to dryness, the filtrate was crystallized from 2 kg of a mixed solvent of dichloromethane: acetonitrile = 1:20 at -10 C, crystallized, filtered, and the filter cake was recrystallized from 2 kg of acetonitrile, crystallized, and filtered to give a filter cake. Under the truthAfter drying, C0P130 is about 628g.(Yield 52.1%, purity 98.6%).

Reference： [1]Patent: CN109400647,2019,A .Location in patent: Paragraph 0056-0063

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Isomers

Technical Information

? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Amines ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

Historical Records

Similar Product of
[ 147127-20-6 ]

A667389[ 1236287-04-9 ]

Tenofovir maleate

Reason: Free-salt

A137641[ 206184-49-8 ]

(R)-(((1-(6-Amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid hydrate

Reason: Hydrate

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 147127-20-6 ] {[proInfo.proName]}

Quality Control of [ 147127-20-6 ]

Related Doc. of [ 147127-20-6 ]

Product Details of [ 147127-20-6 ]

Calculated chemistry of [ 147127-20-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 147127-20-6 ]

Application In Synthesis of [ 147127-20-6 ]

[ 147127-20-6 ] Synthesis Path-Upstream 1~2

[ 147127-20-6 ] Synthesis Path-Downstream 1~5

Technical Information

Similar Product of [ 147127-20-6 ]

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 147127-20-6 ]