Anomeric stereospecific synthesis of 2 '-C-methyl beta-nucleosides; the Holy reaction of cyanamide with 2-C-methyl-D-arabinose

The sequential reactions of 2-C-methyl-d-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at C2′, to give 2′-C-methyl uridine; ring opening with sodium hydroxide gave 2′-C-methyl arabino-uridine with retention of con...

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Bibliographic Details
Main Authors: Jenkinson, S, Jones, N, Moussa, A, Stewart, A, Heinz, T, Fleet, G
Format: Journal article
Language:English
Published: 2007
Description
Summary:The sequential reactions of 2-C-methyl-d-arabinose with cyanamide and methyl propiolate afford an anhydronucleoside, which may be opened under acid conditions with inversion at C2′, to give 2′-C-methyl uridine; ring opening with sodium hydroxide gave 2′-C-methyl arabino-uridine with retention of configuration at C2′. This gives complete stereospecific control to yield only β-nucleosides. © 2007 Elsevier Ltd. All rights reserved.