Method for removing the protecting group for hydroxy group

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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540310, 540347, 540350, C07D48700, C07D49900, C07D48708, C07D48704

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052604381

ABSTRACT:
A method for removing tri-substituted silyl group from .beta.-lactam compound having a tri-substituted silyl group-protecting hydroxy group, which comprises treating with an acid and a fluoride selected from alkali metal fluoride, alkaline earth metal fluoride and hydrogenfluoride of organic or inorganic amine, by which the tri-substituted silyl group can be easily and effectively removed under moderate conditions so that the desired compound can be obtained in high yield at low cost.

REFERENCES:
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S. Hanessian, D. Desilets, Y. Bennani, "A Novel Ring-Closure Strategy for the Carbapenems: The Total thesis of (+)-Thienamycin", J. Org. Chem., 55, 3098-3103 1990.
A. G. M. Barrett, S. Sakadarat, "Total Syntheses of Penicillanic Acid S,S-Dioxide and 6-Aminopenicillanic Acid Using (Benzyloxy)nitromethane", J. Org. Chem., 55, 5110-5117 1990.
M. Imuta, et al. "Carbapenem and Penem Antibiotics. VI. Synthesis and Antibacterial Activity of 2-Heteroaromatic-thiomethys and 2-Carbamoyloxymethyl 1-Methylcarbapenems", Chem. Pharm. Bull. 39(3) 663-671.

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