Method for making steroidal peracyl glycosides

US5530107A · kind A · utility

Assignee

• PFIZER INC. · US

Inventors

• Douglas J. M. Allan · New London, US
• Frank R. Busch · Gales Ferry, US
• John F. Lambert · Preston, US
• Russell J. Shine · Waterford, US
• Stanley W. Walinsky · Mystic, US

Key dates

• Filing date: May 23, 1994
• Grant date: Jun 25, 1996
• Expiry date: May 23, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J71/0005
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

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.