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Model Studies on the Analysis of Pyruvic Acid Acetal-containing Polysaccharides by the Reductive-cleavage Method by Samuel G. Zeller; Gary R. Gray is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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ABSTRACI The 4,6-0-(1-methoxycarbonylethylidene), -(hydroxyisopropylidene), and -(methoxyisopropylidene) acetals of methyl 2,3-di-0-methyl-cw-D-glucopyranoside were subjected to reductive cleavage in the presence of triethylsilane and trimethylsilyl methanesulfonate-boron trifluoride etherate (MesSiOMs-BF, -Et,O), BF, . Et,O, or trimethylsilyl trifluoromethanesulfonate (Me,SiOSO,CF,) and the mole fractions of products were determined as a function of reaction time. The 4,6-(1-methoxycarbonylethylidene) acetal was quite stable to reductive-cleavage conditions but isomerization of the initial R,S mixture of diastereomers to the more-stable S diastereoisomer was noted. In addition, a slow, regiospecific, reductive ring-opening of the acetal was observed to give 6-O-[l-(methoxycarbonyl)ethyl] derivatives. The 4,6-(hydroxyisopropylidene) acetal was very unstable under reductive-cleavage conditions. Both Me,SiOMs-BF,.Et,O and Me,SiOSO,CF, catalyzed complete removal of the group, via the intermediate 6-[1-(hydroxymethyl)ethyl] ether, but BF,.Et,O gave a mixture of products. The 4,6-(methoxyisopropylidene) acetal was also very labile under reductive-cleavage conditions; Me,SiOMs-BF, . Et,0

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Author

Samuel G. Zeller; Gary R. Gray

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1990

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)