5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-ethynyl-8-oxo-7-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-

Base Information

Chemical Name:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-ethynyl-8-oxo-7-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)-
CAS No.:160032-69-9
Molecular Formula:C26H20F3NO8S2
Molecular Weight:595.574
Hs Code.:

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,
3-[(acetyloxy)methyl]-7-ethynyl-8-oxo-7-[[(trifluoromethyl)sulfonyl]oxy]-,
diphenylmethyl ester, (6R,7R)-

Synonyms:

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

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

There total 5 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-ethynyl-8-oxo-7-[[(trifluoromethyl)sulfonyl]oxy]-, diphenylmethyl ester, (6R,7R)- 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: 62.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 160032-68-8
(6R,7R)-3-Acetoxymethyl-7-ethynyl-7-hydroxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 160032-69-9
(6R,7R)-3-Acetoxymethyl-7-ethynyl-8-oxo-7-trifluoromethanesulfonyloxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 0.5h;
DOI:10.1021/ja00103a010

Reference yield:

: 27266-61-1,54600-89-4
benzhydryl 7-aminocephalosporanate

: 160032-69-9
(6R,7R)-3-Acetoxymethyl-7-ethynyl-8-oxo-7-trifluoromethanesulfonyloxy-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: 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

2: 50 percent / C₂HMgBr / tetrahydrofuran / 2.5 h / -78 - -40 °C

3: 62 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; C₂HMgBr; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm970351x

Reference yield:

: 59128-53-9
benzhydryl 7-oxocephalosporanate

: 160032-69-9
(6R,7R)-3-Acetoxymethyl-7-ethynyl-8-oxo-7-trifluoromethanesulfonyloxy-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / C₂HMgBr / tetrahydrofuran / 2.5 h / -78 - -40 °C

2: 62 percent / pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; C₂HMgBr; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm970351x