(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

Base Information

Chemical Name:(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide
CAS No.:97764-69-7
Molecular Formula:C₁₅H₁₉ClN₂O₈S
Molecular Weight:422.843
Hs Code.:

Synonyms:(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

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Chemical Property of (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

Chemical Property:

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Technology Process of (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

There total 8 articles about (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide 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: 86.0%

: 124-63-0
methanesulfonyl chloride

: 92973-23-4
(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-hydroxybutanamide

: 97764-69-7
(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

Guidance literature:: With triethylamine; In 1,2-dimethoxyethane; at -20 - -15 ℃; for 1h;
DOI:10.1021/jo00219a009

Reference yield:

: 92754-75-1
(2S,3R)-2-<(benzyloxycarbonyl)amino>-3-hydroxy-4-butanolide

: 97764-69-7
(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / 25-28 percent ammonia/water / hexane / 3 h / 0 - 5 °C

2: 9.31 percent / N,N-dimethyl-acetamide / 1 h / -25 - -20 °C

3: 72 percent / triethylamine / 1,2-dimethoxy-ethane / 1 h / -25 - -20 °C

With ammonium hydroxide; water; triethylamine; In 1,2-dimethoxyethane; hexane; N,N-dimethyl acetamide;
DOI:10.1248/cpb.33.3798

Reference yield:

: 92973-44-9
2-<(benzyloxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-erythronamide

: 97764-69-7
(2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / aq. HCl / acetonitrile / 2 h / Ambient temperature

2: 76 percent / 2,6-lutidine / dimethylformamide; CH₂Cl₂ / 1.5 h / -10 - 0 °C

3: 86 percent / NEt₃ / 1,2-dimethoxy-ethane / 1 h / -20 - -15 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylamine; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00219a009