(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

Base Information

Chemical Name:(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate
CAS No.:1272318-17-8
Molecular Formula:C₁₉H₂₄N₂O₇
Molecular Weight:392.409
Hs Code.:

Synonyms:(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

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Chemical Property of (2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

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Technology Process of (2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

There total 5 articles about (2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-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: 88.0%

: 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

: 1272318-17-8
(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

Guidance literature:: With boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; for 14h; Sealed tube;
DOI:10.1016/j.tet.2010.12.031

Reference yield:

: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

: 1272318-17-8
(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; triethylamine / chloroform / 18 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / chloroform / 72 h / 20 °C

3: tetrahydrofuran / 20 h / Reflux

4: boron trifluoride diethyl etherate / tetrahydrofuran; diethyl ether / 14 h / Sealed tube

With dmap; boron trifluoride diethyl etherate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; chloroform;
DOI:10.1016/j.tet.2010.12.031

Reference yield:

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

: 1272318-17-8
(2S,3R)-methyl 3-(benzyloxy)-2-((3aS,5R,6S,6aS)-6-hydroxy-2-oxohexahydro-2H-cyclopenta[d]oxazole-5-carboxamido)butanoate

Guidance literature:: Multi-step reaction with 3 steps

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

2: tetrahydrofuran / 20 h / Reflux

3: boron trifluoride diethyl etherate / tetrahydrofuran; diethyl ether / 14 h / Sealed tube

With piperidine; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2010.12.031