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

Base Information

Chemical Name:(3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester
CAS No.:1417557-63-1
Molecular Formula:C₁₈H₂₅FN₄O₃
Molecular Weight:364.42
Hs Code.:

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

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Chemical Property of (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester

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Technology Process of (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester

There total 6 articles about (3R,4S,5S)-3-azido-4-benzyloxy-5-fluoroazepane-1-carboxylic acid-tert-butyl ester 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: 97.0%

: 1417557-66-4
(3R,4S,5S)-3-azido-4-benzyloxy-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

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

Guidance literature:: With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 25 ℃; Reagent/catalyst; Inert atmosphere;
DOI:10.1016/j.tet.2012.10.078

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 110009-21-7,115586-66-8,110044-33-2
(S)-2-((R)-1-benzyloxy-allyl)-oxirane

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

Guidance literature:: Multi-step reaction with 6 steps

1.1: neat (no solvent) / 40 h / 70 °C

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

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

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

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

5.2: 50 °C / Inert atmosphere

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

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