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Branched chain sugars 9. characterization of the stereo isomeric methyl 3 deoxy 3 c methyl 3 nitro pento pyranosides resulting from the condensation of nitro ethane with l methoxy di glycolaldehyde and the x ray crystal structure of methyl 2 4 di o acetyl 3 deoxy 3 c methyl 3 nitro beta d xylo pyranoside



Branched chain sugars 9. characterization of the stereo isomeric methyl 3 deoxy 3 c methyl 3 nitro pento pyranosides resulting from the condensation of nitro ethane with l methoxy di glycolaldehyde and the x ray crystal structure of methyl 2 4 di o acetyl 3 deoxy 3 c methyl 3 nitro beta d xylo pyranoside



Journal of the Chemical Society Perkin Transactions I (4): 995-1002



Base-catalyzed cyclization of the 'dialdehyde' (7) (obtained on periodate oxidation of methyl-.beta.-D-xylopyranoside) with nitroethane gave, after acetylation, a mixture containing 5 of the 8 possible methyl-2,4-di-O-acetyl-3-deoxy-3-C-methyl-3-nitropentopyranosides. The solvolytic behavior of the corresponding methyl-3-acetamido-3-deoxy-2,4-di-O-methanesulfonyl-3-C-methylpentopyranosides and interconversions between the stereoisomers, by way of the monosulfonates (24) and (25), revealed that 4 of the stereoisomers formed in the nitroethane condensation possess .alpha.-L-lyxo, .alpha.-L-xylo, .beta.-D-xylo and .alpha.-L-arabino configurations. The crystal structure of methy-2,4-di-O-acetyl-3-deoxy-3-C-methyl-3-nitro-.beta.-D-xylopyranoside (8) is reported. [Some of the studied compounds are antibiotic components.].

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