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

Base Information

• Chemical Name: tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-1-carboxylate
• CAS No.: 1609349-50-9
• Molecular Formula: C₁₈H₂₆N₄O₅
• Molecular Weight: 378.428
• Mol file: 1609349-50-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-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: 56.0%

(3R,4R)-3-azido-4-benzyloxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester → tert-butyl (3R,4S,5S,6S)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-1-carboxylate (1609349-49-6) + tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-1-carboxylate (1609349-50-9)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 5h;

DOI:10.1002/ejoc.201301811

Reference yield: 96.0%

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

Guidance literature:

With trifluoroacetic acid; at 25 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1071/CH14256

Reference yield: 70.0%

tert-butyl (3R,4S,5R,6R)-3-azido-4-benzyloxy-5,6-dihydroxyazepane-1-carboxylate (1609349-50-9) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-6-(tert-butyldimethylsilyl)oxy-5-hydroxyazepane-1-carboxylate (1609349-51-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301811

Downstream raw materials:

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

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

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

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