3-deoxy-2,5-DI-O-p-nitrobenzoyl-α-D-threo-pentofuranosyl bromide, a starting material for the synthesis of nucleosides

Document Type

Article

Publication Date

1-1-1974

Abstract

Hydrogenation (Raney nickel) of methyl 2,3-anhydro-α- and β-D-lyxo-furanoside (3 and 12) for 12 h at 60 60 lb.in.-2 afforded methyl 3-deoxy-α- and β-D-threo pentofuranoside (4 and 13). These were p-nitrobenzoylated to give the 2,5-di-p-nitrobenzoates (5b and 14b) which, on treatment with hydrogen bromide in acetyl bromide-acetic acid-dichloromethane, afforded the title compound (6b). The structure of compound 4 was established by conversion into the previously prepared 2,5-dibenzoate 5a of known structure, and the anomeric configuration of 6b was established by comparison of its optical rotation and the signals of its anomeric proton with those of methyl 3-deoxy-D-threo-pentofuranosides. © 1974.

Publication Title

Carbohydrate Research

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