(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

Base Information

Chemical Name:(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester
CAS No.:298199-45-8
Molecular Formula:C₂₀H₂₁BrN₄O₅
Molecular Weight:477.315
Hs Code.:

Synonyms:(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

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Chemical Property of (2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

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Technology Process of (2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

There total 4 articles about (2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl 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: 75.0%

: 298199-44-7
(2S,3R)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-6-chlorohexanoate

: 298199-45-8
(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1021/ol0061034

Reference yield:

: 106-41-2
4-bromo-phenol

: 298199-45-8
(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / DCC / DMAP / CH₂Cl₂ / 10 h / 0 - 20 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 0 - 20 °C

2.2: 90 percent / tetrahydrofuran / 1 h / 20 °C

3.1: sodium hydroxide; potassium osmate dihydrate; t-butyl hypochlorite / propan-1-ol / 0.08 h

3.2: (DHQD)2-AQN; potassium osmate dihydrate / propan-1-ol / 4 h / 20 °C

4.1: 75 percent / sodium azide / dimethylformamide / 48 h / 20 °C

With sodium hydroxide; potassium osmate(VI); sodium azide; tert-butylhypochlorite; sodium hydride; dicyclohexyl-carbodiimide; dmap; In tetrahydrofuran; propan-1-ol; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: aminohydroxylation / 3.2: Addition / 4.1: Substitution;
DOI:10.1021/ol0061034

Reference yield:

: 254115-09-8
(para-bromophenyl)-6-chloro-2-(E)-hexenoate

: 298199-45-8
(2S,3R)-6-Azido-2-benzyloxycarbonylamino-3-hydroxy-hexanoic acid 4-bromo-phenyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide; potassium osmate dihydrate; t-butyl hypochlorite / propan-1-ol / 0.08 h

1.2: (DHQD)2-AQN; potassium osmate dihydrate / propan-1-ol / 4 h / 20 °C

2.1: 75 percent / sodium azide / dimethylformamide / 48 h / 20 °C

With sodium hydroxide; potassium osmate(VI); sodium azide; tert-butylhypochlorite; In propan-1-ol; N,N-dimethyl-formamide; 1.1: aminohydroxylation / 1.2: Addition / 2.1: Substitution;
DOI:10.1021/ol0061034