Syntheses of branched-chain sugars with push-pull functionality

✍ Scribed by Klaus Peseke; Holger Feist; Eckehard Cuny

• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 456 KB
• Volume: 230
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)84041-p

✦ Synopsis

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.