(2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide

Base Information

• Chemical Name: (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide
• CAS No.: 213695-83-1
• Molecular Formula: C₂₈H₃₄N₂O₄Si
• Molecular Weight: 490.674
• Mol file: 213695-83-1.mol

Synonyms:(2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide

Chemical Property of (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide

There total 1 articles about (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide 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: 64.0%

benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate (49705-98-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide (213695-83-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.3987/com-98-8152

Reference yield:

(2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide (213695-83-1) → H-L-Thr(TPS)-NH2 (213695-85-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h; Ambient temperature;

DOI:10.3987/com-98-8152

Reference yield:

(2S,3R)-2-benzyloxycarbonylamino-3-(t-butyldiphenylsiloxy)butanamide (213695-83-1) → (2S,3R)-2-{2-[(R)-1-(t-butoxycarbonylamino)-2-methylpropyl]thiazol-4-ylcarbonylamino}-3-(t-butyldiphenylsiloxy)butanamide (213695-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethanol / 4 h / 20 °C

2: 97 percent / diphenoxyphosphinoyl azide; Et₃N / dimethylformamide / 0 - 20 °C

With diphenyl phosphoryl azide; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation;

DOI:10.1246/bcsj.72.2483

upstream raw materials:

benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate

tert-butylchlorodiphenylsilane

Downstream raw materials:

H-L-Thr(TPS)-NH₂

(2S,3R)-2-{2-[(R)-1-(t-butoxycarbonylamino)-2-methylpropyl]thiazol-4-ylcarbonylamino}-3-(t-butyldiphenylsiloxy)butanamide

(2S,3R)-2-{2-[(R)-1-(t-butoxycarbonylamino)-2-methylpropyl]thiazol-4-ylcarbonylamino}-3-(t-butyldiphenylsiloxy)butanethioamide

2-(2-{2-[(1S,2R)-1-{[2-((R)-1-tert-Butoxycarbonylamino-2-methyl-propyl)-thiazole-4-carbonyl]-amino}-2-(tert-butyl-diphenyl-silanyloxy)-propyl]-thiazol-4-yl}-6-formyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester