Crystalline ribofuranosyl halides and other derivatives and meth

Details Crystalline ribofuranosyl halides and other derivatives and meth Crystalline ribofuranosyl halides and other derivatives and meth

1978-10-16

1981-08-04

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536119, 536 55, 536122, C07H 1502, C07H 1518, C07H 1302

Patent

active

042823498

ABSTRACT:
Methyl-D-ribofuranoside is p-nitrobenzoylated to yield crystalline methyl 2,3,5-tri-O-(p-nitrobenzoyl)-.beta.-D-ribofuranoside which can be used to prepare a stable, crystalline 2,3,5-tri-O-(p-nitrobenzoyl)-.beta.-D-ribofuranosyl bromide which in turn is useful as a precursor of natural or synthetic purine and pyrimidine nucleosides, as well as of glycosides. This bromide can also be cyanated to yield crystalline 2,5-anhydro-3,4,6-tri-O-(p-nitrobenzoyl)-D-allononitrile which in turn can be hydrolyzed and subsequently reacted with polyamino pyrimidines to yield nucleoside analogs such as 8-.beta.-D-ribofuranosyl adenine. This bromide also can by hydrolyzed to yield crystalline 2,3,5-tri-O-(p-nitrobenzoyl)-D-ribofuranose which in turn can be p-nitrobenzolated to yield crystalline 1,2,3,5-tetra-O-(p-nitrobenzoyl)-.beta.-D-ribofuranose. This latter compound can be brominated to produce an alphabromide derivative which is useful as a precursor of nucleosides.

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patent: 3501456 (1970-03-01), Shen et al.
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Ness et al. "Chem. Abst.", vol. 75, 1971, p. 141081n.
El Khadem, et al. "Chem. Abst.", vol. 83, 1975, pp. 147,674v.
El Khadem, et al. "Chem. Abst.", vol. 84, 1976, pp. 180,490a.

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