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

Base Information

Chemical Name:tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate
CAS No.:1609349-55-4
Molecular Formula:C₁₈H₂₃F₃N₄O₃
Molecular Weight:400.401
Hs Code.:

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

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

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

There total 6 articles about tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-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: 54.0%

: 1609349-54-3
tert-butyl (3R,4S,5R)-3-azido-4-benzyloxy-5-fluoro-6-oxoazepane-1-carboxylate

: 1609349-55-4
tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate

Guidance literature:: With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 0 ℃; for 10h; Inert atmosphere;
DOI:10.1002/ejoc.201301811

Reference yield:

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

: 1609349-55-4
tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 0 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 25 °C / Inert atmosphere

3: pyridinium chlorochromate / dichloromethane / 25 °C / Inert atmosphere; Molecular sieve

4: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 10 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; pyridinium chlorochromate; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201301811

Reference yield:

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

: 1609349-55-4
tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 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

3: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 0 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 25 °C / Inert atmosphere

5: pyridinium chlorochromate / dichloromethane / 25 °C / Inert atmosphere; Molecular sieve

6: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 10 h / 0 °C / Inert atmosphere

With 1H-imidazole; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; pyridinium chlorochromate; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.201301811