PREPARATION OF TIGOGENIN-; 11-KETOTIGOGENIN-, HECOGENIN-, AND DIOSGENIN-BETA-0-CELLOBIOSIDE HEPTAALKANOATE FROM THE RELEVANT STEROID IN THE PRESENCE OF ZINC FLUORIDE OR CYANIDE

PREPARATION OF TIGOGENIN-; 11-KETOTIGOGENIN-, HECOGENIN-, AND DIOSGENIN-BETA-0-CELLOBIOSIDE HEPTAALKANOATE FROM THE RELEVANT STEROID IN THE PRESENCE OF ZINC FLUORIDE OR CYANIDE

Processes for the synthesis of tigogenin beta-O-cellobioside heptaalkanoate which is an intermediate for the known hypocholesterolemic agent tigogenin beta-cellobioside. The process comprises reacting alpha -cellobiosyl bromide heptaalkanoate and beta -tigogenin in the presence of zinc fluoride or z...

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Bibliographische Detailangaben
Hauptverfasser: BUSCH, FRANK R, ALLEN, DOUGLAS J M, LAMBERT, JOHN F, WALINSKY, STANLEY W, SHINE, RUSSELL J
Format: Patent
Sprache:eng
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APPARATUS THEREFOR
CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
PERFORMING OPERATIONS
PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
STEROIDS
THEIR RELEVANT APPARATUS
TRANSPORTING
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Zusammenfassung:Processes for the synthesis of tigogenin beta-O-cellobioside heptaalkanoate which is an intermediate for the known hypocholesterolemic agent tigogenin beta-cellobioside. The process comprises reacting alpha -cellobiosyl bromide heptaalkanoate and beta -tigogenin in the presence of zinc fluoride or zinc cyanide under conditions capable of forming said tigogenyl beta -O-cellobioside heptaalkanoate. The analogous preparations of hecogenin beta -O-cellobioside heptaalkanoate 11-ketotigogenin beta -O-cellobioside heptaalkanoate, and diosgenin beta -O-cellobioside heptaalkanoate are also disclosed. The process provides both high beta -anomeric selectivity and high yields.