(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

Base Information

Chemical Name:(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate
CAS No.:1272318-12-3
Molecular Formula:C₂₃H₃₂N₂O₇
Molecular Weight:448.516
Hs Code.:

Synonyms:(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

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Chemical Property of (2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

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Technology Process of (2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

There total 6 articles about (2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate 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 (1R,2S,4R,5S)-7-oxo-3-oxa-6-azatricyclo[3.2.1.0]octan-6-carboxylate

: 90072-35-8
(2S,3R)-O-benzyl-threonine methyl ester

: 1272318-12-3
(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

Guidance literature:: In tetrahydrofuran; for 20h; chemoselective reaction; Reflux;
DOI:10.1016/j.tet.2010.12.031

Reference yield:

: 339048-94-1
(2S,3R)-N-Fmoc-O-benzyl-threonine methyl ester

: 1272318-12-3
(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: piperidine / N,N-dimethyl-formamide / 3 h / 20 °C

2: tetrahydrofuran / 20 h / Reflux

With piperidine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2010.12.031

Reference yield:

: 151792-53-9
tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

: 1272318-12-3
(2S,3R)-methyl 3-(benzyloxy)-2-((1S,2R,4S,5R)-4-(tert-butoxycarbonylamino)-6-oxabicyclo [3.1.0] hexane-2-carboxamido)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / chloroform / 72 h / 20 °C

2: tetrahydrofuran / 20 h / Reflux

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform;
DOI:10.1016/j.tet.2010.12.031