(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

Base Information

Chemical Name:(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester
CAS No.:139179-48-9
Molecular Formula:C₂₃H₂₁FN₂O₈S
Molecular Weight:504.493
Hs Code.:

Synonyms:(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

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Chemical Property of (5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

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Technology Process of (5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

There total 9 articles about (5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl 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: 36.0%

: 160154-00-7
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(4-fluoro-benzenesulfonylmethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 139179-48-9
(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 22h;
DOI:10.1016/S0040-4020(01)89561-2

Reference yield:

: 160154-01-8
(2S,5R,6S)-3-[1-(4-Fluoro-benzenesulfonyl)-meth-(Z)-ylidene]-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

: 139179-48-9
(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h; Yield given;
DOI:10.1016/S0040-4020(01)89561-2

Reference yield:

: 619-73-8
4-nitrobenzyl chloride

: 139179-48-9
(5R,6S)-3-<<4-(fluorophenyl)-sulfonyl>methyl>-6-<(1R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylic acid,(4-nitrophenyl)methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / dicyclohexylcarbodiimide, dimethylaminopyridine / tetrahydrofuran

2: 84 percent / iodine, sodium bicarbonate, sodium acetate / H₂O; ethyl acetate / 0.5 h / Irradiation

3: LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

4: 36 percent / n-Bu₄NF, acetic acid / tetrahydrofuran / 22 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; iodine; sodium acetate; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; water; ethyl acetate;
DOI:10.1016/S0040-4020(01)89561-2