Process for the preparation of 2-amino-9-(2,3,5-tri-O-benzyl-bet

Details Process for the preparation of 2-amino-9-(2,3,5-tri-O-benzyl-bet Process for the preparation of 2-amino-9-(2,3,5-tri-O-benzyl-bet

1989-12-04

1992-05-05

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 26, 544264, 544265, C07H 1916, C07H 1919, C07D47300, C07D47302

Patent

active

051109190

ABSTRACT:
A process for the preparation of 2,6-diamino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine (V) by reacting 2,6-di(alkoxyacetamido)purine (II) with 2,3,5-tri-O-benzyl-1-chloro-alpha-D-arabinofuranose (III) to produce 2,6-di(alkoxyacetamido)-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)puri ne (IV) and then deprotecting the 2,6-positions to produce the 2,6-diamine (V) is described. The process provides purine (V) in high yield. Purine (V) is an intermediate in the preparation of 9-beta-D-arabinofuranosyl-2-fluoroadenine which is a cytotoxic agent.

REFERENCES:
patent: 3008969 (1961-11-01), Pretka
patent: 4188378 (1980-02-01), Montgomery
Chemical Abstracts, vol. 104, No. 19, No. 168743j.
Groziak et al. J. Org. Chem. vol. 51, No. 8, pp. 1277-1282.
Montgomery et al., in J. Hetero. Chem. 16, 157 (1979).

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