2",3",4'-tri(acetyl)-4",6"-ethylidine-.beta.-D-glucopyranosides,

Details 2",3",4'-tri(acetyl)-4",6"-ethylidine-.beta.-D-glucopyranosides, 2",3",4'-tri(acetyl)-4",6"-ethylidine-.beta.-D-glucopyranosides,

1993-11-19

1995-01-31

Rollins, John W.

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

Organic compounds

Carbohydrates or derivatives

536 41, 536 185, 536 186, 536115, 536120, C07H 1524

Patent

active

053860160

ABSTRACT:
The invention relates to 2",3",4'-tris(acetyl)-4",6"-ethylidene-.beta.-D-glucopyranosides, their preparation and their use for the preparation of 4'-demethylepipodophyllotoxin ethylidene-.beta.-D-glucopyranoside. The compounds of the invention are of the formula ##STR1## Their process of preparation comprises the following stages: acylation of a glycosyl derivative
acylation of an aglycone
coupling of the acylated glycosyl derivative and the acylated aglycone, in the presence of a Lewis acid, the acylation being carried out using an acid chloride, which is optionally identical for the two stages of acylation, in which the carbon in .alpha. of the carbonyl function bears at least one heteroatom chosen from among O and S.

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McOmie; Protective Groups in Organic Chemistry, pp. 109-118 (1973).
Fock; Chemical Abstracts 96:164565w (1982).

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