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

Base Information

• Chemical Name: (1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic acid tert-butyl ester
• CAS No.: 305837-40-5
• Molecular Formula: C₂₁H₃₆N₂O₅Si
• Molecular Weight: 424.613
• Mol file: 305837-40-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic 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: 99.0%

methyl (2S,3R)-3-[(tert-butyloxycarbonyl)amino]-2-[(tert-butyldimethylsilyl)oxy]-3-(4-methoxyphenyl)propionate (305837-39-2) → (1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (305837-40-5)

Guidance literature:

With ammonia; In methanol; at 25 ℃; for 336h;

DOI:10.1021/ja0212314

Reference yield:

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) → (1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (305837-40-5)

Guidance literature:

Multi-step reaction with 5 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

3.1: H₂ / Pd/C / methanol

4.1: 99 percent / NH₃ gas / methanol / 336 h / 25 °C

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

DOI:10.1021/ja0212314

Reference yield:

methyl (2S,3R)-3-[(benzyloxycarbonyl)amino]-2-hydroxy-3-(4-methoxyphenyl)propionate (305837-37-0) → (1R,2S)-[2-[(tert-butyldimethylsilyl)oxy]-2-carbamoyl-1-(4-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (305837-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 °C

2: H₂ / Pd/C / methanol

3: 99 percent / NH₃ gas / methanol / 336 h / 25 °C

With 2,6-dimethylpyridine; ammonia; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja0212314

upstream raw materials:

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

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

threo-BocCNH-β-OTBDMS

L-threo-BocNH-β-OH-Asn-OBn