(2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Base Information

• Chemical Name: (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester
• CAS No.: 133957-11-6
• Molecular Formula: C₂₉H₃₅NO₅Si
• Molecular Weight: 505.686

Synonyms:(2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property of (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

Chemical Property:

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Technology Process of (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

There total 2 articles about (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl 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: 90.0%

methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate (84449-06-9) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (133957-11-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)80941-8

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (133957-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaHCO₃ / ethyl acetate; H₂O / 24 h / Ambient temperature

2: 90 percent / imidazole / dimethylformamide / 0.5 h / 70 °C

With 1H-imidazole; sodium hydrogencarbonate; In water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80941-8

Reference yield:

(2R,3S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (133957-11-6) → [(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid benzyl ester (133957-01-4)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃;

DOI:10.1016/S0040-4020(01)80941-8

upstream raw materials:

methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

tert-butylchlorodiphenylsilane

benzyl chloroformate

Downstream raw materials:

[(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-formyl-propyl]-carbamic acid benzyl ester

[(1S,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,6S)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester

[(1S,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl)-propyl]-carbamic acid benzyl ester

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