(2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester

Base Information

• Chemical Name: (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester
• CAS No.: 136031-73-7
• Molecular Formula: C₁₃H₁₇N₃O₃
• Molecular Weight: 263.296
• Mol file: 136031-73-7.mol

Synonyms:(2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester

Chemical Property of (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester

There total 4 articles about (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(2R,3S)-3-phenyloxirane-2-carboxylic acid tert-butyl ester (7042-30-0,21309-18-2,27593-40-4,144732-59-2,144732-60-5,136031-72-6) → (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester (136031-73-7)

Guidance literature:

With sodium azide; In water; tert-butyl alcohol; at 50 ℃; for 24h;

DOI:10.1016/0040-4039(91)80631-F

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester (136031-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) a) chiral bromoborane 6, b) triethylamine / 1) a) toluene, hexane, -78 deg C, 1 min, b) 2 h, 2) -78 deg C, 2 h

2: 82 percent / KOt-Bu / 2-methyl-propan-2-ol / 2 h / 20 °C

3: 75 percent / sodium azide / 2-methyl-propan-2-ol; H₂O / 24 h / 50 °C

With sodium azide; chiral bromoborane 6; potassium tert-butylate; triethylamine; In water; tert-butyl alcohol;

DOI:10.1016/0040-4039(91)80631-F

Reference yield:

benzaldehyde (100-52-7) → (2R,3R)-3-Azido-2-hydroxy-3-phenyl-propionic acid tert-butyl ester (136031-73-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) a) chiral bromoborane 6, b) triethylamine / 1) a) toluene, hexane, -78 deg C, 1 min, b) 2 h, 2) -78 deg C, 2 h

2: 82 percent / KOt-Bu / 2-methyl-propan-2-ol / 2 h / 20 °C

3: 75 percent / sodium azide / 2-methyl-propan-2-ol; H₂O / 24 h / 50 °C

With sodium azide; chiral bromoborane 6; potassium tert-butylate; triethylamine; In water; tert-butyl alcohol;

DOI:10.1016/0040-4039(91)80631-F

upstream raw materials:

(2R,3S)-3-phenyloxirane-2-carboxylic acid tert-butyl ester

bromoacetic acid tert-butyl ester

benzaldehyde

t-butyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-phenylpropionate

Downstream raw materials:

tert-butyl (2R,3R)-3-amino-2-hydroxy-3-phenylpropionate