4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7 -oxo-, (4-nitrophenyl)methyl ester, (5R)-

Base Information

Chemical Name:4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7 -oxo-, (4-nitrophenyl)methyl ester, (5R)-
CAS No.:623906-34-3
Molecular Formula:C23H19BrN2O8S2
Molecular Weight:595.448
Hs Code.:

4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,
6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7
-oxo-, (4-nitrophenyl)methyl ester, (5R)-

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Chemical Property of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7 -oxo-, (4-nitrophenyl)methyl ester, (5R)-

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Technology Process of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7 -oxo-, (4-nitrophenyl)methyl ester, (5R)-

There total 5 articles about 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)methyl]-6-bromo-7 -oxo-, (4-nitrophenyl)methyl ester, (5R)- 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: 41.0%

: 623564-80-7
6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde

: 108-24-7
acetic anhydride

: 623564-16-9
(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

: 623906-34-3
6-[acetoxy-(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: 6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde; (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester; With triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 ℃; for 8h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at 0 ℃; for 18h;
DOI:10.1021/jm060021p

Reference yield:

: 4-chloro-2H-pyran-3-carbaldehyde

: 623906-34-3
6-[acetoxy-(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / CH₂Cl₂ / 18 h / Heating

2.1: LiAlH₄ / tetrahydrofuran / 18 h / Heating

3.1: 1.2 g / MnO₂ / CH₂Cl₂ / 1 h / Heating

4.1: MgBr₂; Et₃N / tetrahydrofuran; acetonitrile / 8 h / -20 °C

4.2: 41 percent / tetrahydrofuran; acetonitrile / 18 h / 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; triethylamine; magnesium bromide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm060021p

Reference yield:

: 108-97-4
4-pyrone

: 623906-34-3
6-[acetoxy-(6,7-dihydro-4H-thieno[3,2-c]pyran-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: POCl₃ / CH₂Cl₂ / 2 h / 0 °C

2.1: Et₃N / CH₂Cl₂ / 18 h / Heating

3.1: LiAlH₄ / tetrahydrofuran / 18 h / Heating

4.1: 1.2 g / MnO₂ / CH₂Cl₂ / 1 h / Heating

5.1: MgBr₂; Et₃N / tetrahydrofuran; acetonitrile / 8 h / -20 °C

5.2: 41 percent / tetrahydrofuran; acetonitrile / 18 h / 0 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; triethylamine; magnesium bromide; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Vilsmier-Hack reaction;
DOI:10.1021/jm060021p