Synthesis of 1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-[(R) and (S) -methoxyphosphinyl]-alpha- and -beta-D-ribopyranoses.
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.
D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
D003855:Deoxyribose