Syntheses of branched-chain sugars with push-pull functionality.
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.
Peseke
K
K
Fachbereich Chemie, Universität Rostock, Germany.
Feist
H
H
Cuny
E
E
D002236:Carbohydrate Conformation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*; D009904:Optical Rotation
D007202:Indicators and Reagents; D009005:Monosaccharides