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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| creator | BUSCH, FRANK R ALLEN, DOUGLAS J M LAMBERT, JOHN F WALINSKY, STANLEY W SHINE, RUSSELL J |
| description | 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. |
| format | Patent |
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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. 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| subjects | 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 |
| title | PREPARATION OF TIGOGENIN-; 11-KETOTIGOGENIN-, HECOGENIN-, AND DIOSGENIN-BETA-0-CELLOBIOSIDE HEPTAALKANOATE FROM THE RELEVANT STEROID IN THE PRESENCE OF ZINC FLUORIDE OR CYANIDE |
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