5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-, diphenylmethyl ester, (6R,7Z)-

Base Information

Chemical Name:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-, diphenylmethyl ester, (6R,7Z)-
CAS No.:162252-98-4
Molecular Formula:C29H29NO7S
Molecular Weight:535.618
Hs Code.:
Mol file:162252-98-4.mol

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,
3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-,
diphenylmethyl ester, (6R,7Z)-

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Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-, diphenylmethyl ester, (6R,7Z)-

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Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-, diphenylmethyl ester, (6R,7Z)-

There total 7 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[2-(1,1-dimethylethoxy)-2-oxoethylidene]-8-oxo-, diphenylmethyl ester, (6R,7Z)- 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: 55.0%

: 59128-53-9
benzhydryl 7-oxocephalosporanate

: 86302-43-4,35000-38-5
(tert-Butoxycarbonylmethylene)triphenylphosphorane

: 162252-98-4
(R)-3-Acetoxymethyl-7-[1-tert-butoxycarbonyl-meth-(Z)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jm00006a022

Reference yield: 55.0%

: 59128-53-9
benzhydryl 7-oxocephalosporanate

: [(tert-butoxycarbonyl)methylene]triphenylphosphorane

: 162252-98-4
(R)-3-Acetoxymethyl-7-[1-tert-butoxycarbonyl-meth-(Z)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jm970351x

Reference yield:

: 908093-98-1
diazodiphenylmethane

: 162252-98-4
(R)-3-Acetoxymethyl-7-[1-tert-butoxycarbonyl-meth-(Z)-ylidene]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 41 percent / methanol; CH₂Cl₂ / 44 h / Ambient temperature

2: 1.) Tf₂O, Et₃N, 2.) aq. HCl / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 30 min

3: 55 percent / CH₂Cl₂ / 0.5 h / -78 °C

With hydrogenchloride; trifluoromethylsulfonic anhydride; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jm970351x