(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
CAS No.:99333-79-6
Molecular Formula:C₂₁H₂₃F₃N₂O₈S
Molecular Weight:520.483
Hs Code.:

Synonyms:(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Chemical Property of (6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Technology Process of (6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 7 articles about (6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl 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: 75.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 99333-78-5
(6R,7S)-7-tert-Butoxycarbonylamino-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

: 99333-79-6
(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In chloroform; at 0 ℃;
DOI:10.1016/S0040-4039(00)89251-5

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 99333-79-6
(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran; H₂O / pH 7

2: 1.) ozone, Sudan III, 2.) Me₂S

3: 94 percent / tosyl azide, Hunig's base / acetonitrile

4: 72 percent / titanium tetrabenzyloxide / 42 h / 36 °C

5: Rh₂OAc₄ / 0.33 h

6: 75 percent / Hunig's base / CHCl₃ / 0 °C

With 4-toluenesulfonyl azide; dimethylsulfide; oil scarlet; ozone; N-ethyl-N,N-diisopropylamine; dirhodium tetraacetate; titanium tetrakis(benzyl alkoxide); In tetrahydrofuran; chloroform; water; acetonitrile;
DOI:10.1016/S0040-4039(00)89251-5

Reference yield:

: 99333-73-0
(3S,4R)-3-Amino-4-[2-(5-methoxy-cyclohexa-1,4-dienyl)-ethyl]-azetidin-2-one

: 99333-79-6
(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran; H₂O / pH 7

2: 1.) ozone, Sudan III, 2.) Me₂S

3: 94 percent / tosyl azide, Hunig's base / acetonitrile

4: 72 percent / titanium tetrabenzyloxide / 42 h / 36 °C

5: Rh₂OAc₄ / 0.33 h

6: 75 percent / Hunig's base / CHCl₃ / 0 °C

With 4-toluenesulfonyl azide; dimethylsulfide; oil scarlet; ozone; N-ethyl-N,N-diisopropylamine; dirhodium tetraacetate; titanium tetrakis(benzyl alkoxide); In tetrahydrofuran; chloroform; water; acetonitrile;
DOI:10.1016/S0040-4039(00)89251-5