Convenient synthesis of 2,3-O-isopropylidene-5-thio-D-ribose and 5-thio-D-ribose; Synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-D-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-D-ribopyranose

Abstract

Sequential mesylation-acetylation of 2,3-O-isopropylidene-D-ribofuranose gave 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-β-D-ribofuranose that was converted into 1-O-acetyl-5-(S)-acetyl-2,3-O-isopropylidene-5-thio-β-D-ribose, deacetylation of which gave 2,3-O-isopropylidene-5-thio-D-ribose as the β-pyranose form, which was hydrolysed to 5-thio-D-ribose. 1,4-Anhydro-2,3-O-isopropylidene-α-D-ribopyranose was obtained by sodium methoxide treatment of 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-β-D-ribofuranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-D-ribopyranose was similarly synthesised via 1-(S)-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-5-thio-α-D-ribofuranose. Copyright (C) 1999 Elsevier Science Ltd.