diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide

Base Information

• Chemical Name: diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide
• CAS No.: 91618-44-9
• Molecular Formula: C₂₉H₃₉NO₅SSi
• Molecular Weight: 541.784

Synonyms:diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide

Chemical Property of diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide

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Technology Process of diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide

There total 1 articles about diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide 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%

(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (129544-00-9) → diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide (91618-44-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 5 ℃; for 3h; Cooling;

DOI:10.3987/COM-08-S(N)110

Reference yield: 72.0%

diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide (91618-44-9) + 2,2-dimethylpropanoic anhydride (1538-75-6) → (3S,4R)-4-(pivaloylthio)-3-[(1'(R)-tert-butyldimethylsiloxy)ethyl]-N-[2-methyl-1-(diphenylmethyl)oxycarbonyl-2-propenyl]-2-azetidinone + (3S,4R)-4-(pivaloyloxy)-3-[(1'(R)-tert-butyldimethylsiloxy)ethyl]-N-[2-methyl-1-(diphenylmethyl)oxycarbonyl-2-propenyl]-2-azetidinone

Guidance literature:

With triethyl phosphite; In 1,2-dichloro-ethane; at 82 ℃; for 30h; Inert atmosphere;

DOI:10.3987/COM-08-S(N)110

Reference yield: 62.0%

diphenylmethyl (3S,5R,6S)-6-[(1'(R)-tert-butyldimethylsilyloxy)ethyl]penicillanate 1β-sulfoxide (91618-44-9) + acetic anhydride (108-24-7) → (3S,4R)-4-(acetylthio)-3-[(1'(R)-tert-butyldimethylsiloxy)ethyl]-N-[2-methyl-1-(diphenylmethyl)oxycarbonyl-2-propenyl]-2-azetidinone + (3S,4R)-4-(acethoxy)-3-[(1'(R)-tert-butyldimethylsiloxy)ethyl]-N-[{2-methyl-1-(diphenylmethyl)oxycarbonyl}propenyl]-2-azetidinone

Guidance literature:

With triethyl phosphite; In benzene; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.3987/COM-08-S(N)110

upstream raw materials:

(2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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