methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate

Base Information

• Chemical Name: methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate
• CAS No.: 305837-38-1
• Molecular Formula: C₂₅H₃₅NO₆Si
• Molecular Weight: 473.642
• Mol file: 305837-38-1.mol

Synonyms:methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate

Chemical Property of methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate

There total 2 articles about methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate 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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(4-methoxyphenyl)propionate (305837-37-0) → methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate (305837-38-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2.5h;

DOI:10.1021/ja0212314

Reference yield:

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) → methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate (305837-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOH; tert-butyl hypochlorite; (DHQD)2PHAL / propan-1-ol; H₂O

1.2: 71 percent / K₂OsO₂(OH)4 / propan-1-ol; H₂O / 2 h / 0 °C

2.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 °C

With 2,6-dimethylpyridine; sodium hydroxide; tert-butylhypochlorite; 1,4-bis(9-O-dihydroquinidine)phthalazine; In propan-1-ol; dichloromethane; water; 1.1: Sharpless asymmetric aminohydroxylation;

DOI:10.1021/ja0212314

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate (305837-38-1) → methyl (2S,3R)-3-[(tert-butyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate (305837-39-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; for 6h; under 760.051 Torr;

DOI:10.1021/jo000628s

upstream raw materials:

t-butyldimethylsiyl triflate

methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(4-methoxyphenyl)propionate

3-(4-methoxy-phenyl)acrylic acid methyl ester

Downstream raw materials:

methyl (2S,3R)-3-[(tert-butyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate

(1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic acid tert-butyl ester

threo-BocCNH-β-OTBDMS