(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

Base Information

Chemical Name:(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
CAS No.:160154-01-8
Molecular Formula:C₂₃H₂₁FN₂O₈S
Molecular Weight:504.493
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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:

: 160226-42-6
(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[1-(4-fluoro-benzenesulfonyl)-meth-(Z)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

: 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

Guidance literature:: With hydrogen fluoride; In acetonitrile; for 3h;
DOI:10.1016/S0040-4020(01)89561-2

Reference yield:

: 619-73-8
4-nitrobenzyl chloride

: 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

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

4: HF / acetonitrile / 3 h

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

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 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

Guidance literature:: Multi-step reaction with 6 steps

1: 66.9 percent / zinc, diethylaluminum chloride / tetrahydrofuran; toluene / 0 degC, 2 h, room t., overnight

2: 90 percent / sodium hydride / tetrahydrofuran; dimethylformamide / Ambient temperature

3: 76 percent / dicyclohexylcarbodiimide, dimethylaminopyridine / tetrahydrofuran

4: 84 percent / iodine, sodium bicarbonate, sodium acetate / H₂O; ethyl acetate / 0.5 h / Irradiation

5: 58 percent / LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C

6: HF / acetonitrile / 3 h

With dmap; hydrogen fluoride; iodine; sodium acetate; diethylaluminium chloride; sodium hydride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)89561-2