Intermediates for the preparation of demethylepipodophyllotoxin
AssigneeSocieta Italiana Cortico-Steroidi S.p.A.
InventorsPietro Allevi, Mario Anastasia, Ettore Bigatti, Peter MacDonald
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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.
Claims7
In the process for the preparation of demethylepipodophyllotoxin-.beta.-glucosides in which a glucose derivative and a demethylepipodophyllotoxin derivative are allowed to react in the presence of a Lewis acid, the improvement which comprises allowing a glucose derivative of the formula:
- ##STR5## in which the two R.sup.1 groups together are alkylidene, arylalkylidene, or heteroarylalkylidene, R.sup.2 is lower alkanoyl or haloacetyl, and R.sup.3 is trialkylsilyl, to react with demethylepipodophyllotoxin.
Dependencies are inferred from the claim text.