(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

Base Information

Chemical Name:(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane
CAS No.:1417557-64-2
Molecular Formula:C₁₃H₁₇FN₄O
Molecular Weight:264.303
Hs Code.:

Synonyms:(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

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Chemical Property of (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

Chemical Property:

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Technology Process of (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

There total 7 articles about (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane 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:

: 1417557-63-1
(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester

: 1417557-64-2
(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

Guidance literature:: With trifluoroacetic acid; at 25 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1016/j.tet.2012.10.078

Reference yield:

: 263889-20-9
(2S,3R)-allyl-(3-benzyloxy-2-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester

: 1417557-64-2
(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

Guidance literature:: Multi-step reaction with 5 steps

1.1: Grubbs catalyst first generation / dichloromethane / 42 h / Inert atmosphere; Reflux

2.1: triphenylphosphine; diphenyl phosphoryl azide; diethylazodicarboxylate / tetrahydrofuran / 4.5 h / 25 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 14 h / 25 °C / Inert atmosphere

3.2: 50 °C / Inert atmosphere

4.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 25 °C / Inert atmosphere

5.1: trifluoroacetic acid / 0.08 h / 25 °C / Inert atmosphere

With Grubbs catalyst first generation; borane-THF; diphenyl phosphoryl azide; triphenylphosphine; trifluoroacetic acid; (bis-(2-methoxyethyl)amino)sulfur trufluoride; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2012.10.078

Reference yield:

: 263889-19-6
(2S,3R)-1-allylamino-3-benzyloxy-pent-4-en-2-ol

: 1417557-64-2
(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 42 h / Inert atmosphere; Reflux

3.1: triphenylphosphine; diphenyl phosphoryl azide; diethylazodicarboxylate / tetrahydrofuran / 4.5 h / 25 °C / Inert atmosphere

4.1: borane-THF / tetrahydrofuran / 14 h / 25 °C / Inert atmosphere

4.2: 50 °C / Inert atmosphere

5.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 25 °C / Inert atmosphere

6.1: trifluoroacetic acid / 0.08 h / 25 °C / Inert atmosphere

With Grubbs catalyst first generation; borane-THF; diphenyl phosphoryl azide; triethylamine; triphenylphosphine; trifluoroacetic acid; (bis-(2-methoxyethyl)amino)sulfur trufluoride; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2012.10.078