Synthesis of 1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-[(R) and (S) -methoxyphosphinyl]-alpha- and -beta-D-ribopyranoses |
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| Authors: | H Yamamoto M Harada S Inokawa K Seo M A Armour T T Nakashima |
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| Institution: | Department of Chemistry, Faculty of Science, Okayama University, Okayama 700 Japan;Department of Industrial Chemistry, Numazu Technical College, Numazu 410 Japan;Department of Chemistry, The University of Alberta, Edmonton, Alberta T6G 2G2 Canada |
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| Abstract: | Treatment of methyl 5-deoxy-5-C-( diethoxyphosphinyl )-2,3-O-isopropylidene-beta-D- ri bofuranoside with sodium dihydrobis (2- methoxyethoxy ) aluminate , followed by hydrogen peroxide, mineral acid, and hydrogen peroxide, gave 5-deoxy-5-C-( hydroxyphosphinyl )-alpha,beta-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, 1H-n.m.r. spectra of the title compounds, derived by treatment with diazomethane and then acetic anhydride in pyridine. |
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| Keywords: | To whom correspondence should be addressed |
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