tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate

Base Information

• Chemical Name: tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate
• CAS No.: 887128-09-8
• Molecular Formula: C₂₁H₃₇NO₄Si
• Molecular Weight: 395.615
• Mol file: 887128-09-8.mol

Synonyms:tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate

Chemical Property of tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate

There total 5 articles about tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate 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: 95.0%

methyl (2R)-2-[benzyl(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsilyloxy)propanoate (887128-08-7) → tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate (887128-09-8)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; ethanol; at 20 ℃; Inert atmosphere;

DOI:10.3998/ark.5550190.0011.910

Reference yield: 56.0%

methyl (2R)-2-[benzyl(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsilyloxy)propanoate (887128-08-7) → benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-carbamic acid tert-butyl ester + tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate (887128-09-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1515/HC.2005.11.3-4.343

Reference yield:

methyl (2R)-2-[benzyl(tert-butoxycarbonyl)amino]-3-hydroxypropanoate (887128-07-6) → tert-butyl N-benzyl-N-[(1S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-hydroxyethyl]carbamate (887128-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N; DMAP / CH₂Cl₂

2: 56 percent / LiAlH₄ / tetrahydrofuran

With dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1515/HC.2005.11.3-4.343

upstream raw materials:

methyl (2R)-2-[benzyl(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsilyloxy)propanoate

methyl (2R)-2-[benzyl(tert-butoxycarbonyl)amino]-3-hydroxypropanoate

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

benzaldehyde