(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine
CAS No.:1354826-71-3
Molecular Formula:C₃₇H₄₀FNO₃
Molecular Weight:565.728
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

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Chemical Property of (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

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Technology Process of (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

There total 4 articles about (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine 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: 63.0%

: 1354826-63-3
(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol

: 1354826-73-5
(2S,3S,4R,5S,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-fluoroazepane

: 1354826-71-3
(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

Guidance literature:: With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 4 ℃; for 12.5h;
DOI:10.1021/ol203385w

Reference yield:

: 1354826-56-4
(3R,4R,5R,6S,7S) 7-allyl-4,5,6-tris(benzyloxy)azepan-3-ol

: 1354826-73-5
(2S,3S,4R,5S,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-fluoroazepane

: 1354826-71-3
(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

2: diethylamino-sulfur trifluoride / dichloromethane / 12.5 h / 0 - 4 °C

With diethylamino-sulfur trifluoride; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol203385w

Reference yield:

: 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α,β-D-glucopyranose

: 1354826-73-5
(2S,3S,4R,5S,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-fluoroazepane

: 1354826-71-3
(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine

Guidance literature:: Multi-step reaction with 4 steps

1: solid supported triphenylphosphine / tetrahydrofuran / 40 °C

2: tetrahydrofuran / 1 h / 0 - 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

4: diethylamino-sulfur trifluoride / dichloromethane / 12.5 h / 0 - 4 °C

With diethylamino-sulfur trifluoride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Staudinger/aza-wittig alkylation;
DOI:10.1021/ol203385w