Intermediates for the preparation of demethylepipodophyllotoxin

Details Intermediates for the preparation of demethylepipodophyllotoxin Intermediates for the preparation of demethylepipodophyllotoxin

1995-05-15

1997-11-18

Kight, John

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 181, C07H 100, C07H 2300

Patent

active

056889259

ABSTRACT:
Demethylepipodophyllotoxin-.beta.-glucosides are prepared by allowing demethylepipodophyllotoxin to react with a 2,3-di-O-ester of a 1-O-trialkylsilyl-4,6-O-alkylidene-.beta.-D-glucose derivative in the presence of a Lewis acid. The 4,6-O-alkylidene group can be alkylidene, arylalkylidene, or heteroarylalkylidene and the 2,3-ester can be lower alkanoyl or haloacetyl. In a typical embodiment, demethylepipodophyllotoxin is allowed to react with 4,6-O-ethylidene-2,3-di-O-acetyl-1-O-trimethylsilyl-.beta.-D-glucose in the presence of boron trifluoride etherate to yield etoposide 2",3"-diacetate.

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Lolonde and Chan, Synthesis, pp. 817-843, (1985).

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