methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate

Base Information

• Chemical Name: methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate
• CAS No.: 87305-52-0
• Molecular Formula: C₁₇H₁₈N₂O₄
• Molecular Weight: 314.341

Synonyms:methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate

Chemical Property of methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate

Chemical Property:

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Technology Process of methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate

There total 4 articles about methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate 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: 80.0%

6α-(2-phenyl-acetylamino)-penicillanic acid methyl ester (21794-95-6) → methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate (87305-52-0)

Guidance literature:

With magnesium chloride; In methanol; tert-butyl alcohol; at -40 ℃; electrolysis, Pt electrodes, 10 mA/cm²;

DOI:10.1002/bscb.19820911202

Reference yield: 60.0%

(2R,3S)-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamido-4oxoazetidine-2-sulphinic acid (62607-61-8,63183-66-4) → methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate (87305-52-0)

Guidance literature:

With lead(IV) acetate; In dichloromethane;

DOI:10.1016/S0040-4039(00)81674-3

Reference yield:

C19H22N2O5S2 (87259-80-1) → methyl 2-<(1R,5S)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate (87305-52-0) + 2-((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester (87305-51-9)

Guidance literature:

With triphenylphosphine; In dichloromethane; Yield given;

DOI:10.1016/S0040-4039(00)81674-3

upstream raw materials:

6α-(2-phenyl-acetylamino)-penicillanic acid methyl ester

C₁₉H₂₂N₂O₅S₂

(2R,3S)-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamido-4oxoazetidine-2-sulphinic acid

methyl benzylpenicillinate 1,1-dioxide

Downstream raw materials:

methyl 2-(2,4-dioxo-3-phenylacatamidoazetidin-1-yl)-3-methylbut-2-enoate

2-((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester

methyl 3-methyl-2-<(3R,4R)-2-oxo-3-phenylacetamido-4-pyruvoyloxyazetidin-1-yl>but-2-enoate

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