Syntheses of branched-chain sugars with push-pull functionality.

K Peseke; H Feist; E Cuny

doi:10.1016/0008-6215(92)84041-p

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Syntheses of branched-chain sugars with push-pull functionality.

K Peseke·H Feist·E Cuny

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Abstract

The reaction of methyl 4,6-O-benzylidene-3(2)-deoxy-alpha-D-erythro- hexopyranosid-2(3)-ulose with carbon disulfide, alkyl iodide, and sodium hydride gave methyl 4,6-O-benzylidene-3(2)-[bis(alkylthio)methylene]-3(2)-deoxy-alpha-D- erythro-hexopyranosid-2(3)-uloses. Methyl 4,6-O-benzylidene-2-[bis(methylthio)-methylene]-2-deoxy-alpha-D- erythro-hexopyranosid-3-ulose (5) reacted with aromatic amines to give, in a rearrangement process, N-aryl-2-aryliminomethyl-4,6-O-benzylidene-2-deoxy- alpha-D-erythro-hex-1-enopy-ranosylamin-3-uloses. The reaction of 5 with hydrazine hydrate afforded 5-methylthio-(methyl 4,6-O-benzylidene-2,3-dideoxy-alpha-D-erythro-hexopyranosido)[3,2- c]pyrazole.

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Carbohydrate Conformation Indicators and Reagents Magnetic Resonance Spectroscopy Molecular Structure Monosaccharides Optical Rotation Journal Article Research Support, Non-U.S. Gov't

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K Peseke, H Feist, E Cuny. 1992-06-16. Syntheses of branched-chain sugars with push-pull functionality.. https://doi.org/10.1016/0008-6215(92)84041-p

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