(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
CAS No.:76227-89-9
Molecular Formula:C₂₁H₁₈N₂O₅S
Molecular Weight:410.45
Hs Code.:

Synonyms:(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

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Chemical Property of (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

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Technology Process of (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 8 articles about (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 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: 31.0%

: 76227-86-6,78855-25-1,78855-26-2
2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monobenzyl ester

: 76227-89-9
(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:: With diisopropyl-carbodiimide; In dichloromethane; at -60 - 20 ℃;
DOI:10.1016/S0040-4039(00)77414-4

Reference yield:

: 69-57-8
Penicillin G sodium

: 76227-89-9
2-oxo-bisnorpenicillin G-3-benzyl carboxylate

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) NaH / 1) DMF, 0 deg C; 2) DMF, 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: 94 percent / HCl / CH₂Cl₂; methanol; H₂O / 0.5 h / Ambient temperature

7: 31 percent / N,N-diisopropylcarbodiimide / CH₂Cl₂ / 5 h / -60 deg C -> r.t.

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

Reference yield:

: 76227-78-6
2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-benzyl acetate

: 76227-89-9
2-oxo-bisnorpenicillin G-3-benzyl carboxylate

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: 94 percent / HCl / CH₂Cl₂; methanol; H₂O / 0.5 h / Ambient temperature

3: 31 percent / N,N-diisopropylcarbodiimide / CH₂Cl₂ / 5 h / -60 deg C -> r.t.

With hydrogenchloride; lithium hexamethyldisilazane; diisopropyl-carbodiimide; In methanol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)92143-X