2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

Base Information

Chemical Name:2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate
CAS No.:78815-01-7
Molecular Formula:C₂₀H₂₁Cl₃N₂O₅S
Molecular Weight:507.822
Hs Code.:

Synonyms:

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Chemical Property of 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

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Technology Process of 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

There total 7 articles about 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate 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: 87.0%

: 115-20-8
1,1,1-trichloroethanol

: 76227-84-4,78854-98-5,78855-22-8
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-t-butyl malonate

: 78815-01-7,78854-97-4
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

Guidance literature:: With diisopropyl-carbodiimide; dmap; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(01)92143-X

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 78815-01-7,78854-97-4
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

Guidance literature:: Multi-step reaction with 3 steps

1: 1) Triton B / 1) DMF, CH₃OH, -30 deg C, 15 min; 0 deg C, 15 min; 2) DMF, 15 min, -30 deg C; 1 h, 0 deg C; 2 h, r. t.

2: 1) lithium hexamethyldisilazide-ether 1:1 complex / 1) THF, -60 deg C, 30 min; 2) -60 deg C, 30 min, without cooling, 1 h

3: 87 percent / N,N-diisopropylcarbodiimide / DMAP / CH₂Cl₂ / 1 h / 0 °C

With N-benzyl-trimethylammonium hydroxide; lithium hexamethyldisilazane; diisopropyl-carbodiimide; dmap; In dichloromethane;
DOI:10.1016/S0040-4020(01)92143-X

Reference yield:

: 69-57-8
Penicillin G sodium

: 78815-01-7,78854-97-4
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl and β-trichloroethyl malonate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaIO₄ / 1) H₂O; 2) NEt₃, DMF, 20 deg C

2: 65 percent Chromat_. / MgSO₄, (CH₃O)3P / benzene / 40 h / Heating

3: 74 percent / KMnO₄, MgSO₄ / H₂O; ethanol / 15 - 20 °C

4: 1) Triton B / 1) DMF, CH₃OH, -30 deg C, 15 min; 0 deg C, 15 min; 2) DMF, 15 min, -30 deg C; 1 h, 0 deg C; 2 h, r. t.

5: 1) lithium hexamethyldisilazide-ether 1:1 complex / 1) THF, -60 deg C, 30 min; 2) -60 deg C, 30 min, without cooling, 1 h

6: 87 percent / N,N-diisopropylcarbodiimide / DMAP / CH₂Cl₂ / 1 h / 0 °C

With potassium permanganate; sodium periodate; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; lithium hexamethyldisilazane; diisopropyl-carbodiimide; phosphorous acid trimethyl ester; dmap; In ethanol; dichloromethane; water; benzene;
DOI:10.1016/S0040-4020(01)92143-X