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Synthesis of 1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-[(R) and (S)-methoxyphosphinyl]-α- and -β-d-ribopyranoses

✍ Scribed by Hiroshi Yamamoto; Masahiko Harada; Saburo Inokawa; Kuniaki Seo; Margaret-Ann Armour; Thomas T. Nakashima

Publisher: Elsevier Science
Year: 1984
Tongue: English
Weight: 534 KB
Volume: 127
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(84)85104-6

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✦ Synopsis

Treatment

of methyl 5-deoxy-S-C-(diethoxyphosphinyl)-2.3-O-isopropylidene-p-D-ribofuranoside with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, gave 5deoxy-5-C-(hydroxyphosphinyl)-a,P-D-ribopyranoses in 40-45% overall yield. The structures of these sugar analogs were effectively established on the basis of the mass and 400-MHz, 'H-n.m.r. spectra of the title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine.

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