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- W2069726669 abstract "Arylbis(arylthio)sulfonium salts have been used to activate glycals towards nucleophilic addition to form principally 2-deoxy-β-glycosides. This method was applied to the synthesis of the 2-(methylphenylthio)-2′-phenylthio derivative (22) of methyl O-(4-O-benzyl-2,6-dideoxy-β-d-arabino-hexopyranosyl)-(1 → 3)-3,4-di-O-benzyl-2,6-dideoxy-2,6-β-d-arabino-hexopyranoside, the C′D′ ring analog of an aureolic acid disaccharide. The condensation of 1,5-anhydro-2,6-dideoxy-d-arabino-hex-1-enitol with methanol in the presence of the phenylbis(phenylthio)sulfonium salt resulted in formation of the first β-glycoside linkage. The methyl 6-deoxyglucoside obtained was deprotected at HO-3 to give the 2-thiophenyl-substituted 2,6-dideoxy-β-glucoside. This was coupled with 1,5-anhydro-3,4-di-O-benzyl-2-deoxy-d-arabino-hex-1-enitol in the presence of 4-methylphenyl[bis(4-methylphenyl)thio]sulfonium salt to give the (1 → 3)-linked disaccharide 22. Finally, desulfurization of 22 using WII Raney nickel generated the required 2,2′-dideoxydisaccharide." @default.
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- W2069726669 date "1993-02-01" @default.
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- W2069726669 title "Synthesis of the C′D′ disaccharide of aureolic acid" @default.
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- W2069726669 doi "https://doi.org/10.1016/0008-6215(93)84204-j" @default.
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