diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

Base Information

Chemical Name:diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide
CAS No.:98376-20-6
Molecular Formula:C₂₈H₂₅BrN₂O₆S₂
Molecular Weight:629.552
Hs Code.:

Synonyms:diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

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Chemical Property of diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

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Technology Process of diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

There total 8 articles about diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide 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: 27.0%

: 39098-97-0
2-thienylacetic acid chloride

: 98376-16-0
diphenylmethyl(1S,6R,7S)-7-amino-3-bromomethyl-7-methoxyceph-3-em-4-carboxylate-1-oxide hydrobromide

: 98376-20-6
diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

Guidance literature:: With magnesium oxide; methyloxirane; In dichloromethane; at 0 ℃; for 5.5h;
DOI:10.1016/S0040-4020(01)96571-8

Reference yield:

: 33748-47-9
diphenylmethyl(6R,7R)-7-formamido-3-methylceph-3-em-4-carboxylate

: 98376-20-6
diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / peracetic acid / 1,2-dichloro-ethane / 0.5 h

2: 60 percent / NaOAc, HOAc, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) / CH₂Cl₂; H₂O / 0.67 h / -10 °C / Irradiation; pH=7

3: 77 percent / PBr₃ / CH₂Cl₂ / 1 h / -20 °C

4: LiOMe, t-butyl hypochlorite / tetrahydrofuran / 0.1 h / -70 °C

5: 90percent m-chloroperbenzoic acid / 1.) -20 deg C, 5 min; 2.) up to RT, 1 h

6: 90 percent / PBr₃ / diethyl ether; methanol / 1 h / 0 °C

7: 27 percent / propylene oxide, MgO / CH₂Cl₂ / 5.5 h / 0 °C

With peracetic acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; tert-butylhypochlorite; lithium methanolate; sodium acetate; magnesium oxide; phosphorus tribromide; acetic acid; 3-chloro-benzenecarboperoxoic acid; methyloxirane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4020(01)96571-8

Reference yield:

: 33748-49-1
diphenylmethyl(6R,7R)-3-bromomethyl-7-formamido-ceph-3-em-4-carboxylate

: 98376-20-6
diphenylmethyl(1S,6R,7S)-3-bromomethyl-7-methoxy-7-(thien-2-yl)acetamidoceph-3-em-4-carboxylate-1-oxide

Guidance literature:: Multi-step reaction with 4 steps

1: LiOMe, t-butyl hypochlorite / tetrahydrofuran / 0.1 h / -70 °C

2: 90percent m-chloroperbenzoic acid / 1.) -20 deg C, 5 min; 2.) up to RT, 1 h

3: 90 percent / PBr₃ / diethyl ether; methanol / 1 h / 0 °C

4: 27 percent / propylene oxide, MgO / CH₂Cl₂ / 5.5 h / 0 °C

With tert-butylhypochlorite; lithium methanolate; magnesium oxide; phosphorus tribromide; 3-chloro-benzenecarboperoxoic acid; methyloxirane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)96571-8