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[ CAS No. 565-71-9 ] {[proInfo.proName]}

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Chemical Structure| 565-71-9
Chemical Structure| 565-71-9
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Quality Control of [ 565-71-9 ]

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Product Details of [ 565-71-9 ]

CAS No. :565-71-9 MDL No. :MFCD00008138
Formula : C3H7NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BMYNFMYTOJXKLE-UHFFFAOYSA-N
M.W : 105.09 Pubchem ID :11267
Synonyms :
Chemical Name :DL-Isoserine

Calculated chemistry of [ 565-71-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 22.18
TPSA : 83.55 ?2

Pharmacokinetics

GI absorption : High
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) : -9.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.11
Log Po/w (XLOGP3) : -4.05
Log Po/w (WLOGP) : -1.61
Log Po/w (MLOGP) : -1.7
Log Po/w (SILICOS-IT) : -1.45
Consensus Log Po/w : -1.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 2.19
Solubility : 16300.0 mg/ml ; 156.0 mol/l
Class : Highly soluble
Log S (Ali) : 2.9
Solubility : 82900.0 mg/ml ; 789.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.3
Solubility : 2080.0 mg/ml ; 19.8 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 565-71-9 ]

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

Application In Synthesis of [ 565-71-9 ]

* 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.

  • Downstream synthetic route of [ 565-71-9 ]

[ 565-71-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 565-71-9 ]
  • [ 24424-99-5 ]
  • [ 52558-24-4 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 9h; (S)-isoserine 15a (21 g, 0.20 mol) was dissolved in tetrahydrofuran (100 mL)And a mixed solvent of 10percent aqueous sodium hydroxide solution (100 mL),Di-tert-butyl dicarbonate (50 mL, 0.22 mol) was added dropwise.The reaction was carried out at room temperature for 9 hours.The aqueous phase was adjusted to pH 2 with 4 mol/L hydrochloric acid, and extracted with dichloromethane/methanol (v/v = 5/1, 50 mL × 3) and dried over anhydrous sodium sulfate.Filter by suction, concentrate under reduced pressure,The title compound 15b was obtained as a colorless oil (35 g, yield: 85percent).
81.5% To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H2O (100 mL, 1:1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by BoC2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to O0C and sat aq. NaHCO3 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHSO4. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SO4, filtered and concentrated to dryness to give the desired N-Boc-3-ammo-2(S)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (IOO MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
81.5% To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H20 (100 mL, 1 :1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by Boc20 (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHC03 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHS04. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2S04, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(S)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
81.5% To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: 3/40 (100 mL, 1:1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by B0C2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHC<3/4 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHS04. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SC filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): [H NM (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
81.5% With 4-methyl-morpholine; In 1,4-dioxane; water; at 0 - 20℃; N-Boc-3-amino-2(S)-hydroxy-propionic acid ; <n="62"/>To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H2O (100 mL, 1 :1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by BoC2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHCO3 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHSO4. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SO4, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
81.5% N-Boc-3-amino-2 (^-hydroxy-propionic acid OHTo a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H2O (100 mL, 1 :1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by BoC2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHCO3 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHSO4. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SO4, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
81.5% With 4-methyl-morpholine; In 1,4-dioxane; water; at 0 - 20℃; N-Boc-3-amino-2(5)-hydroxy-propionic acid To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H2O (100 mL, 1:1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by BoC2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHCO3 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHSO4. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SO4, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
80% Part I - Synthesis of (S)-3-((ter^butoxycarbonyl)amino)-2-hydroxypropanoic acid [0261] To (L)-isoserine (1.0 g, 9.5 mmol) in tetrahydrofuran (10 mL) and 2M sodium hydroxide (9.75 mL, 19.5 mmol) was added di-tert-butyl dicarbonate (0.78 g, 10 mmol). The resulting mixture was stirred vigorously at ambient temperature overnight. Then, the reaction mixture was acidified with 1M hydrogen chloride (20 mL) and stirred for 20 minutes until gas evolution ceased. The resulting mixture was partitioned between ethyl acetate and water, washed with brine, dried with sodium sulfate, filtered and concentrated in vacuo to yield title compound. (1.57 g, 80percent yield)
To a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H20 (100 mL, 1 : 1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by Boc20 (1 1.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHC03 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHS04. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2S04, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.

  • 2
  • [ 565-71-9 ]
  • [ 24424-99-5 ]
  • [ 56-40-6 ]
  • [ 52558-24-4 ]
YieldReaction ConditionsOperation in experiment
81.5% N-Boc-3-amino-2 (^-hydroxy-propionic acid OHTo a stirring solution of S-isoserine (4.0 g, 0.038 mol) in dioxane: H2O (100 mL, 1 :1 v/v) at 0° C was added N-methylmorpholine (4.77 mL, 0.043 mol), followed by BoC2O (11.28 mL, 0.049 mol) and the reaction was stirred overnight with gradual warming to room temperature. Glycine (1.0 g, 0.013 mol) was then added and the reaction was stirred for 20 min. The reaction was cooled to 0°C and sat aq. NaHCO3 (75 mL) was added. The aqueous layer was washed with ethyl acetate (2 x 60 mL) and then acidified to pH 1 with NaHSO4. This solution was then extracted with ethyl acetate (3 x 70 mL) and these combined organic layers were dried over Na2SO4, filtered and concentrated to dryness to give the desired N-Boc-3-amino-2(5)-hydroxy- propanoic acid (6.30 g, 0.031 mmol, 81.5 percent yield): 1H NMR (400 MHz, CDC13) delta 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m, 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H); 13C NMR (100 MHz, CDC13) delta 174.72, 158.17, 82, 71.85, 44.28, 28.45.
  • 3
  • [ 565-71-9 ]
  • [ 1455091-10-7 ]
  • [ 1455086-89-1 ]
YieldReaction ConditionsOperation in experiment
92% With sodium methylate; In methanol; at 120℃; for 1h;Microwave irradiation; A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester(90 mg, 0.31 mmol) and 2-(S)-hydroxy-3-amino-propionic acid (Sigma-Aldrich) (96 mg, 0.92 mmol) in 0.5 N NaOMe in MeOH solution (1.22 mL, 0.61 mmol) was microwaved at 120 °C for 1 h and concentrated. Residue was dissolved in water (70 mL) and acidified by 1 N HC1 solution to pH = 3-4. It was extracted with EtOAc, Organic layer was washed with brine, dried over MgSO/t, filtered and concentrated to give the title compound (105 mg, 0.29 mmol) in 92percent yield. LC-MS ESI-: 366.99 (M- 1)-.
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