benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

Base Information

Chemical Name:benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate
CAS No.:147486-90-6
Molecular Formula:C₃₆H₃₀F₃NO₆S₂Si
Molecular Weight:721.85
Hs Code.:

Synonyms:benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

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Chemical Property of benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

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Technology Process of benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

There total 5 articles about benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate 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: 74.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 147486-89-3
benzyl 6α-<(triphenylsilyl)ethynyl>-6β-hydroxypenicillinate

: 147486-90-6
benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

Guidance literature:: With pyridine; In chloroform; Ambient temperature;
DOI:10.1021/jo00058a008

Reference yield:

: 15058-64-7
6-α-hydroxypenicillanic acid

: 147486-90-6
benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) Et₃N / 1) DMF, 0 deg C, 2) rt, overnight

2: 98 percent / trifluoroacetic anhydride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

3: 1) EtMgBr / 1) THF, a) -78 deg C, 5 min, b) -78 deg C to rt, 30 min, 2) THF, -78 deg C to -40 deg C, 30 min

4: 74 percent / pyridine / CHCl₃ / Ambient temperature

With pyridine; ethylmagnesium bromide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; chloroform;
DOI:10.1021/jo00058a008

Reference yield:

: 551-16-6
6-Aminopenicillanic Acid

: 147486-90-6
benzyl 6α-<(triphenylsilyl)ethynyl>-6β-(trifluoromethanesulfonato)penicillinate

Guidance literature:: Multi-step reaction with 5 steps

1: 32 percent / 70percent HClO₄, NaNO₂ / H₂O / 0.33 h / -5 - 0 °C

2: 1) Et₃N / 1) DMF, 0 deg C, 2) rt, overnight

3: 98 percent / trifluoroacetic anhydride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

4: 1) EtMgBr / 1) THF, a) -78 deg C, 5 min, b) -78 deg C to rt, 30 min, 2) THF, -78 deg C to -40 deg C, 30 min

5: 74 percent / pyridine / CHCl₃ / Ambient temperature

With pyridine; perchloric acid; ethylmagnesium bromide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; sodium nitrite; In dichloromethane; chloroform; water;
DOI:10.1021/jo00058a008