tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

Base Information

Chemical Name:tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate
CAS No.:174283-00-2
Molecular Formula:C₂₀H₃₅NO₄Si
Molecular Weight:381.588
Hs Code.:

Synonyms:tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

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Chemical Property of tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

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Technology Process of tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

There total 6 articles about tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate 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: 90.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1219933-95-5
(1S,2R)-1-(benzylamino)-3-(tert-butyldimethylsilyloxy)-1-phenylpropan-2-ol

: 174283-00-2
tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 12h; under 760.051 Torr;
DOI:10.1016/j.tetasy.2009.12.010

Reference yield: 73.0%

: 174282-99-6
(2R,3S)-1-tert-butyldimethylsilyloxy-3-tert-butoxycarbonylamino-2-p-nitrophenylcarbonyloxy-3-phenylpropane

: 174283-00-2
tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -20 ℃; for 3h;
DOI:10.1016/0957-4166(95)00442-4

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 174283-00-2
tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / H₂ / 20percent Pd(OH)2/C / ethyl acetate / 760 Torr

2: 89 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 71 percent / PPh₃, DEAD / benzene / 12 h / Ambient temperature

4: 73 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -20 °C

With 1H-imidazole; hydrogen; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0957-4166(95)00442-4