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• W2004809093 abstract "Abstract Base-catalyzed addition of nitromethane to the 2-ethyl hemialdal 3 , resulting from the reversible addition of ethanol to the dialdehyde 2 obtained from NaIO 4 oxidation of methyl 4,6- O -benzylidene-α- D -glucopyranoside ( 1 ) in aqueous solution, yields four main isomeric 3-nitroheptoseptanosides having respectively the D - glycero - D - manno ( 7 , 42%), D - glycero - D - ido ( 5 , 36%), D - glycero - D - galacto ( 6 , 12%) and D - glycero - D - talo ( 9 , 7 equilibrated slowly in pyridine with the D - glycero - D - altro isomer 11 , whereas, under similar conditions, 6 underwent a fast epimerization to the D - glycero - D - gulo isomer ( 10 ). Equilibration of 5 in the presence of an excess of sodium methoxide afforded a 3:2 mixture of 9 and 7 , whereas conversely action of catalytic proportion of the same base on 9 produced 5 . The configuration at C-2C-4 for the series of nitroheptoseptanosides have been assigned by conversion into the corresponding methyl 3-acetamido-3-deoxyheptopyranosides and then into known 3-amino-3-deoxyhexose derivatives. Tentative correlations have been drawn between the stereochemistry in the transiion state for the addition of the nitroalkyl carbanion, the conformation of the resulting seven-membered ring and its nitronate, and the relative distribution and stability of epimeric nitroheptoseptanosides obtained in the reaction. Conformational preferences for nitroheptoseptanosides, as inferred from 1 H-n.m.r. data, are discussed. Comparative NaIO 4 oxidations were performed on methyl 4,6,- O -benzylidene-β- D -glucopyranoside ( 43 ) resulting in the formation of the corresponding C-2C-3 dialdehyde 44 isolated as its 2-ethyl hemialdal 45 . Base-catalyzed nitromethane addition to 45 resulted in the formation of at least three isomeric nitroheptoseptanosides with respective configurations D - glycero - D - altro , D - glycero - D - gluco , and D - glycero - D - galacto which were identified mostly by comparison of their 13 C-n.m.r. parameters with compounds obtained in the α- D series." @default.
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• W2004809093 date "1991-06-01" @default.
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• W2004809093 title "Structure and reactions of amino- and nitro-heptoseptanosides obtained by cyclization of dialdehydes with nitromethane" @default.
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