tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

Base Information

Chemical Name:tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate
CAS No.:1609349-51-0
Molecular Formula:C₂₄H₄₀N₄O₅Si
Molecular Weight:492.691
Hs Code.:

Synonyms:tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

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Chemical Property of tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

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Technology Process of tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

There total 2 articles about tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate 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: 70.0%

: 1609349-50-9
tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-1-carboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1609349-51-0
tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201301811

Reference yield:

: (3R,4R)-3-azido-4-benzyloxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester

: 1609349-51-0
tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water / 5 h / 20 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 25 °C / Inert atmosphere

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.201301811

Reference yield: 69.0%

: 1609349-51-0
tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate

: 1609349-52-1
tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-fluoroazepane-1-carboxylate

Guidance literature:: With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 0 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201301811