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

Base Information

• Chemical Name: tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate
• CAS No.: 1609349-53-2
• Molecular Formula: C₁₈H₂₅FN₄O₄
• Molecular Weight: 380.419
• Mol file: 1609349-53-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-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: 75.0%

tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-fluoroazepane-1-carboxylate (1609349-52-1) → tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate (1609349-53-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201301811

Reference yield: 71.0%

tert-butyl (3R,4S,5R)-3-azido-4-benzyloxy-5-fluoro-6-oxoazepane-1-carboxylate (1609349-54-3) → tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate (1609349-53-2) + (3R,4S,5S,6S)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylic acid tert-butyl ester

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 1.5h;

DOI:10.1071/CH14256

Reference yield:

(3R,4R)-3-azido-4-benzyloxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester → tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate (1609349-53-2)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; osmium(VIII) oxide; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.201301811

upstream raw materials:

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

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

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

Downstream raw materials:

(4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

(4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane

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

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