[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 217661-62-6
• Molecular Formula: C₂₀H₃₅NO₄Si
• Molecular Weight: 381.588
• Mol file: 217661-62-6.mol

Synonyms:[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester

There total 5 articles about [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-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:

tert-butyldimethylsilyl chloride (18162-48-6) + ((1R,2R)-2-hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester (1009093-14-4) → [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester (217661-62-6)

Guidance literature:

With 1H-imidazole; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 20 ℃; for 19h;

Reference yield:

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate (124085-68-3) + phenylmagnesium bromide (100-58-3) → [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester (217661-62-6)

Guidance literature:

phenylmagnesium bromide; With titanium(IV) isopropylate; In diethyl ether; dichloromethane; at -78 ℃;

tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.orglett.5b03292

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester (217661-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 2 h

2: 1H-imidazole / dimethyl sulfoxide; N,N-dimethyl-formamide / 19 h / 20 °C

With 1H-imidazole; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

phenylmagnesium bromide

tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-hydroxypropan-2-yl carbamate

tert-butyldimethylsilyl chloride

((1R,2R)-2-hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester

Downstream raw materials:

C₂₈H₃₈N₂O₅Si

(2R,3R)-N-Boc-3-methoxy-1-O-(tert-butyldimethylsilyl)-phenylalaninol

(2R,3R)-N-Boc-3-methoxy-phenylalaninol

(2S,3R)-N-(tert-butyloxycarbonyl)-3-methoxyphenylalanine