Process of preparing etoposide phosphate and etoposide

Details Process of preparing etoposide phosphate and etoposide Process of preparing etoposide phosphate and etoposide

1993-11-04

1995-10-17

Robinson, Douglas W.

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

Organic compounds

Carbohydrates or derivatives

536 41, 536 171, 536115, 536117, 536120, A61K 3170, C07H 1524

Patent

active

054592488

ABSTRACT:
Etoposide phosphate is prepared by coupling dibenzyl 4'-demethyl-4-epipodophyllotoxin-4'-phosphate with 2,3-di-O-benzyl-4,6-O-ethylidene-.alpha.,.beta.-D-glucopyranose in a solvent and subsequently removing the protecting groups. The tetra-benzyl protected etoposide phosphate is recrystallized from methanol or directly crystallized from acetonitrile by adding methanol to yield substantially the pure C-1"-.beta. form. The benzyl protecting groups are simultaneously removed by hydrogenation to produce etoposide phosphate in high yields. In a further embodiment, etoposide phosphate is treated with a phosphatase enzyme to yield etoposide.

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