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[ CAS No. 14464-29-0 ] {[proInfo.proName]}

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Chemical Structure| 14464-29-0

Chemical Structure| 14464-29-0

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Quality Control of [ 14464-29-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 14464-29-0 ]

CAS No. :	14464-29-0	MDL No. :	MFCD00037916
Formula :	C₆H₇NO₄	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	SIFCHNIAAPMMKG-UHFFFAOYSA-N
M.W :	157.12	Pubchem ID :	84460
Synonyms :

Safety of [ 14464-29-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14464-29-0 ]

* 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 [ 14464-29-0 ]
Downstream synthetic route of [ 14464-29-0 ]

[ 14464-29-0 ] Synthesis Path-Upstream 1~1

1
[ 14464-29-0 ]
[ 692-04-6 ]

Reference： [1] Patent: CN109265371, 2019, A, . Location in patent: Paragraph 0026-0028

[ 14464-29-0 ] Synthesis Path-Downstream 1~10

1
[ 6066-82-6 ]
[ 64-19-7 ]
[ 14464-29-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dicyclohexyl-carbodiimide; In 1,4-dioxane; at 5 - 20℃; for 20h;	2.2 ml (25 mmol) DCCD was added at 5C to a solution of 1.43 ml (25 mmol) acetic acid and 2.2 ml (0.25 mmol)N-hydroxysuccinimide in 50 ml dioxane. The reaction mixture was stirred at 20C for 20 h. The resulting precipitate wasfiltered off and washed with dry dioxane. The filtrates were combined and evaporated to yield 3.65 g (93%) of the productas white crystals. Rf 0.41 (C), Rf 0.75 (I); m.p. 103-105C. 1H NMR (DMSO-d6): 2.34 (3H, s, -CH3CO-), 2.80 (4H, m, -CH2CH2- OSu).
	With 1,2-dichloro-ethane; In dichloromethane; for 3h;	General procedure: To a stirred solution of appropriate acid 44a-f (1.96mmol) in CH2Cl2 (3mL) were added NHS (0.361g, 3.14mmol) and EDC (0.601g, 3.14mmol). After 3h, the mixture was diluted with CH2Cl2 (40mL). The organic layer was washed with brine (2×40mL), saturated aqueous NaHCO3 (40mL) and brine (2×40mL), dried over Na2SO4, filtered and concentrated to give NHS activated esters (80-100% yield) that were used immediately without further purification.
	With dicyclohexyl-carbodiimide; In ethyl acetate; at 20℃;Inert atmosphere;	The syntheses of GlcNAc and GlcNGc from glucosamine were based on the method described by Lapidot [31]. The procedure for the synthesis of GlcNAc was performed as follows: acetic acid (0.286 mL, 5 mmol) was added to a solution of N-hydroxysuccinimide (0.575 g, 5 mmol) in dry ethyl acetate (23 mL). A solution of dicyclohexylcarbodiimide (1.03 g, 5 mmol) in ethyl acetate (2 mL)was then added. The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere. Then, the precipitate of the reaction mixture was removed by centrifugation at 13,400 g for 10 min. The supernatant contained an NHS-ester of acetic acid was dried by rotary evaporation under reduced pressure and re-dissolved in dry 17 mL of methanol. D-Glucosamine hydrochloride(0.862 g, 4 mmol) and triethylamine (0.56 mL) were then added and dissolved by placing the sample ina heated sonication bath (50 C for 1 h). The reaction mixture was then stirred at room temperature for 16 h. The sample was again dried using rotary evaporation and washed three times with ethyl acetate(1 mL) to remove the unreacted starting material. After vacuum drying of the sample using centrifugal evaporation, the product was dissolved in 8 mL of 10% methanol in water (v/v). The supernatant was collected and concentrated using a rotary evaporator under reduced pressure. For the synthesisof GlcNGc, glycolic acid (0.3 mL, 5 mmol) was used instead of acetic acid. As judged by TLC analysis, the conversion of D-glucosamine to the reaction products 4a or 4b reached approximately 70%. These amidated reaction products were then used directly as starting material for the enzymatic sialylation reactions.

Reference： [1]Patent: EP2397488,2019,B1 .Location in patent: Paragraph 0181; 0182
[2]Journal of the Chemical Society. Chemical communications,1985,p. 473
[3]Journal of Medicinal Chemistry,2000,vol. 43,p. 2938 - 2945
[4]Tetrahedron,1998,vol. 54,p. 3489 - 3494
[5]Journal of Molecular Structure,1992,vol. 273,p. 215 - 226
[6]European Journal of Medicinal Chemistry,2017,vol. 138,p. 13 - 25
[7]Molecules,2019,vol. 24

2
[ 6066-82-6 ]
[ 75-36-5 ]
[ 14464-29-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 146 - 151
[2]Tetrahedron,1997,vol. 53,p. 15225 - 15236

3
[ 14464-29-0 ]
[ 2037-48-1 ]
[ 51587-80-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2186 - 2208

4
[ 14464-29-0 ]
[ 1078691-95-8 ]
N-acetylglucosamine-6-phosphate barium salt [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 146 - 151

5
[ 14464-29-0 ]
C₁₈H₂₈N₄O₇S [ No CAS ]
[ 121903-84-2 ]
[ 129624-97-1 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 3813 - 3818

6
[ 866102-80-9 ]
[ 14464-29-0 ]
2-(dimethylamino)ethyl 4-[4-(acetylamino)butyl]amino}benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5805 - 5812

7
[ 14464-29-0 ]
[ 371123-22-7 ]
[ 128960-84-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2300 - 2313

8
[ 14464-29-0 ]
[ 55533-24-9 ]
[ 114117-42-9 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 6834 - 6835

9
N-(3-aminopropyl)-N'-anthracen-9-ylmethyl-N'-ethylpropane-1,3-diamine [ No CAS ]
[ 14464-29-0 ]
N-{3-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propyl}-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate; In dichloromethane; at 0 - 20℃; for 8.66667h;	A saturated sodium carbonate solution (20 mL) was added to a vigorously stirred solution of 7a (250 mg, 0.55 mmol) in CH2Cl2 (20 mL). The organic layer was separated and was washed twice with saturated sodium carbonate. The combined organic layers were dried with anhydrous Na2SO4, filtered and concentrated to give the free amine 22 as a pale yellow oil in 99percent yield. 22: 1H NMR (CDCl3) delta 8.48 (d, 2H), 8.38 (s, 1H), 7.97 (d, 2H), 7.47 (m, 4H), 4.47 (s, 2H), 2.70 (q, 2H), 2.51 (m, 4H), 2.29 (t, 2H), 2.17 (t, 2H), 1.56 (q, 2H), 1.24 (m, 5H); 13C NMR (CDCl3): 6 131.5, 131.4, 130.9, 129.1, 127.4, 125.6, 125.5, 125.2, 124.9, 50.8, 50.7, 48.3, 47.8, 40.7, 33.7, 27.0, 12.0. A mixture of compound 22 (190 mg, 0.54 mmol) and anhydrous K2CO3 (113 mg, 0.82 mmol) in anhydrous CH2Cl2 was stirred at 0° C. for 10 minutes. N-Acetoxysuccinimide (NHS ester, 60 mg, 0.38 mmol) was dissolved in dry CH2Cl2 and was added slowly to the above stirred solution at 0° C. under N2 atmosphere. The mixture was then stirred for 30 minutes at 0° C. and then slowly allowed to come at room temperature and stirred for 8 hrs. After the confirmation of the disappearance of the ester by TLC in CH2Cl2/hexane (7:3), the solution was filtered and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 23 as a light yellow oil. Yield 67percent; Rf=0.30 (7percent MeOH: 1percent NH4OH: 82percent CH2Cl2); 1H NMR (CDCl3) delta 8.43 (d, 2H), 8.35 (s, 1H), 7.95 (d, 2H), 7.23 (m, 4H), 6.84 (br t, 1H), 4.43 (s, 2H), 3.05 (q, 2H), 2.71 (q, 2H), 2.43 (t, 2H), 2.20 (t, 2H), 2.09 (t, 2H), 2.78 (s, 3H), 2.48 (q, 2H), 1.21 (m, 5H); 13C NMR (CDCl3) delta 170.0, 131.4, 131.3, 130.6, 129.1, 127.5, 125.7, 124.9, 124.9, 50.6, 48.1, 48.0, 48.0, 39.0, 28.2, 26.6, 23.4, 11.8. HRMS (FAB) m/z calcd. for C25H33N3O (M+H)+ 392.2701, found 392.2709.

Reference： [1]Patent: US2007/213397,2007,A1 .Location in patent: Page/Page column 6

10
C₂₅H₃₅N₆O₉P [ No CAS ]
[ 14464-29-0 ]
C₂₉H₃₉N₆O₁₁P [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 4751 - 4753

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Code	Phrase
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Code	Phrase
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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:
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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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