(3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid

Base Information

• Chemical Name: (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid
• CAS No.: 1373825-53-6
• Molecular Formula: C₁₈H₂₉NO₅Si
• Molecular Weight: 367.517
• Mol file: 1373825-53-6.mol

Synonyms:(3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid

Chemical Property of (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid

There total 3 articles about (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid (119221-16-8) → (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid (1373825-53-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 24h;

DOI:10.1016/j.ejmech.2017.02.036

Reference yield:

Z-Thr-OH + tert-butyldimethylsilyl chloride (18162-48-6) → (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid (1373825-53-6) + (2S,3R)-2-(benzyloxycarbonylamino)-3-tertiary-butyldimethylsilyloxybutanoic acid (94820-26-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 18h; optical yield given as %ee;

DOI:10.1021/jo300527f

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid (1373825-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water / 18 h / 20 °C

2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 18 h / 20 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide;

DOI:10.1021/jo300527f

upstream raw materials:

tert-butyldimethylsilyl chloride

benzyl chloroformate

(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid