2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-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>-mono-β-trichloroethyl malonate
CAS No.:78815-04-0
Molecular Formula:C₁₆H₁₃Cl₃N₂O₅S
Molecular Weight:451.715
Hs Code.:

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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>-mono-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>-mono-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>-mono-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: 100.0%

: 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

: 78815-04-0,78855-01-3
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-β-trichloroethyl malonate

Guidance literature:: With hydrogen bromide; In dichloromethane; at 0 ℃; for 2h; 1 h, 15 deg C;
DOI:10.1016/S0040-4020(01)92143-X

Reference yield:

: 69-57-8
Penicillin G sodium

: 78815-04-0,78855-01-3
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-β-trichloroethyl malonate

Guidance literature:: Multi-step reaction with 7 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

7: 100 percent / HBr / CH₂Cl₂ / 2 h / 0 °C / 1 h, 15 deg C

With potassium permanganate; sodium periodate; hydrogen bromide; 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

Reference yield:

: 76227-79-7
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate

: 78815-04-0,78855-01-3
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-β-trichloroethyl malonate

Guidance literature:: Multi-step reaction with 3 steps

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

2: 87 percent / N,N-diisopropylcarbodiimide / DMAP / CH₂Cl₂ / 1 h / 0 °C

3: 100 percent / HBr / CH₂Cl₂ / 2 h / 0 °C / 1 h, 15 deg C

With hydrogen bromide; lithium hexamethyldisilazane; diisopropyl-carbodiimide; dmap; In dichloromethane;
DOI:10.1016/S0040-4020(01)92143-X