6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

Base Information

Chemical Name:6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester
CAS No.:93756-63-9
Molecular Formula:C₂₂H₃₁NO₆SSi
Molecular Weight:465.643
Hs Code.:

Synonyms:6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

Chemical Property:

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Technology Process of 6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

There total 2 articles about 6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic 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: 85.0%

: 108-24-7
acetic anhydride

: 93756-62-8
6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-hydroxypenicillanic acid benzyl ester

: 93756-63-9
6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

Guidance literature:: With dmap; triethylamine; at 25 ℃; for 4h;
DOI:10.1021/jo00201a004

Reference yield:

: 39126-59-5
6-oxopenicillanic acid benzyl ester

: 93756-63-9
6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) sec-butyllithium / 1.) THF, cyclohexane, -23 deg C, 15 min, 2.) -78 deg C, 3 h

2: 85 percent / Et₃N, 4-(dimethylamino)pyridine / 4 h / 25 °C

With dmap; sec.-butyllithium; triethylamine;
DOI:10.1021/jo00201a004

Reference yield:

: 93756-63-9
6α-<(S)-methoxy(trimethylsilyl)methyl>-6β-acetoxypenicillanic acid benzyl ester

: 93756-58-2
6-<(Z)-methoxymethylene>penicillanic acid benzyl ester

: 93756-61-7
6-<(E)-methoxymethylene>penicillanic acid benzyl ester

Guidance literature:: With cesium fluoride; In dimethyl sulfoxide; at 80 ℃; for 2h; Yield given. Yields of byproduct given;
DOI:10.1021/jo00201a004