(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

Base Information

Chemical Name:(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester
CAS No.:124994-64-5
Molecular Formula:C₂₂H₂₁N₃O₇S
Molecular Weight:471.491
Hs Code.:

Synonyms:(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

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Chemical Property of (2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

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Technology Process of (2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

There total 3 articles about (2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl 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: 67.0%

: 124994-63-4
(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid

: 100-11-8
1-bromomethyl-4-nitro-benzene

: 124994-64-5
(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

Guidance literature:: With sodium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; for 16h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89088-8

Reference yield:

: 58578-45-3
(2S)-2-(benzyloxycarbonylamino)-4-oxobutyric acid benzyl ester

: 124994-64-5
(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / 1.) 20 deg C, 3 h 2.) reflux, 15 h

2: 86 percent / lithium hydride monohydrate / tetrahydrofuran / 6 h / 5 - 10 °C

3: 67 percent / NaHCO₃ / NaI / dimethylformamide / 16 h / Ambient temperature

With lithium hydride; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89088-8

Reference yield:

: 109429-17-6
(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid methyl ester

: 124994-64-5
(2S,5R,7S)-1-aza-7-benzyloxycarbonylamino-8-oxo-4-thiabicyclo<3.3.0>octane-2-carboxylic acid p-nitrobenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / lithium hydride monohydrate / tetrahydrofuran / 6 h / 5 - 10 °C

2: 67 percent / NaHCO₃ / NaI / dimethylformamide / 16 h / Ambient temperature

With lithium hydride; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89088-8