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Synthesis of 1,2,4-tri-O-acetyl-5-deoxy-3-O-methyl-5-C-[(R)- and -(S)-phenylphosphinyl]-β-d-ribopyranose

✍ Scribed by Kuniaki Seo

Publisher: Elsevier Science
Year: 1983
Tongue: English
Weight: 297 KB
Volume: 122
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(83)88408-0

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✦ Synopsis

5-Dcoxy-J,2-O-isopropylidene-S-C-(methoxyphenylphosphinyl)-~-O-~~thyl-n-D-ribofuranose (4) was prepared from 1,2-0-isopropylidene-3-O-methyl-a-D-ribo-pentodialdo-1,4-furanose by an addition reaction with methyl phenylphosphinate, followed by deoxygenation of the terminal HO-$H-P group of the adduct by successive reaction with l,l'-thiocarbonyldiimidazole and tributyltin hydride. Treatment of 4 with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by deacetonation with mineral acid, and acetylation with acetic anhydride-pyridine, gave mainly the two title compounds, whichwere isolated by column chromatography onsilicagel,andcharacterizedby90-MHz,'H-n.m.r.-spectralanalysis.

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