(2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol

Base Information

• Chemical Name: (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol
• CAS No.: 425622-85-1
• Molecular Formula: C₂₁H₃₇NO₄Si
• Molecular Weight: 395.615
• Mol file: 425622-85-1.mol

Synonyms:(2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol

Chemical Property of (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol

There total 8 articles about (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol 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%

tert-butyldimethylsilyl chloride (18162-48-6) + ((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester (99113-35-6) → (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol (425622-85-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(01)01152-8

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol (425622-85-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 525 mg / ethyldiisopropylamine / tetrahydrofuran / 2 h / 60 °C

2: 94 percent / H₂ / Pd(OH)2 / methanol / 5 h / 20 °C / atmospheric pressure

3: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01152-8

Reference yield:

phenylmagnesium bromide (1589-82-8) → (2R,3S)-3-(tert-butoxycarbonylamino)-1-(tert-butyldimethylsilyloxy)-4-phenylbutan-2-ol (425622-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / diethyl ether / -30 °C

2: H₂ / Pd(OH)2/C / ethanol / 20 °C / 760 Torr

3: 525 mg / ethyldiisopropylamine / tetrahydrofuran / 2 h / 60 °C

4: 94 percent / H₂ / Pd(OH)2 / methanol / 5 h / 20 °C / atmospheric pressure

5: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01152-8

upstream raw materials:

tert-butyldimethylsilyl chloride

((1S,2R)-1-benzyl-2,3-dihydroxypropyl)carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

phenylmagnesium bromide

Downstream raw materials:

methanesulfonic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenyl-propyl ester

1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane