(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

Base Information

Chemical Name:(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane
CAS No.:479490-53-4
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

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Chemical Property of (2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

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Technology Process of (2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

There total 5 articles about (2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane 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: 53.0%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 254909-27-8
(2R,5S)-7-ethoxycarbonyl-2-phenyl-1-aza-3-oxa-lbicyclo<3.3.0>octan-8-one

: 479490-53-4
(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

: (2R,5S,7R)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

Guidance literature:: (2R,5S)-7-ethoxycarbonyl-2-phenyl-1-aza-3-oxa-lbicyclo<3.3.0>octan-8-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1039/b503994k

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 479490-53-4
(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 4 steps

1: NaN(TMS)2 / tetrahydrofuran / 1.5 h / -5 - 0 °C

2: tetrahydrofuran / 1.5 h / 20 °C

3: aq. NaOH / acetonitrile / 18 h / 20 °C

4: toluene / 2 h / Heating

With sodium hydroxide; sodium hexamethyldisilazane; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1021/jo020433f

Reference yield:

: 479490-65-8
6-tert-butoxycarbonylmethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester

: 479490-53-4
(2R,5S,7S)-7-(tert-butyloxycarbonylmethyl)-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaOH / acetonitrile / 18 h / 20 °C

2: toluene / 2 h / Heating

With sodium hydroxide; In toluene; acetonitrile;
DOI:10.1021/jo020433f