Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Syntheses of Mannosidic Disaccharides from Derivatives of Ethylthio $\alpha$-D-Mannopyranoside

  • Published : 1998.11.20
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Abstract

Derivatives of ethylthio α-D-mannopyranoside as glycosyl donors are compared in coupling efficiency and stercoselectivity with varying thiophilic promoters from methyl triflate (MeOTf), dimethyl(methylthio)sulfonium triflate (DMTST) to iodonium dicollidine perchlorate (IDCP), solvents and glycosyl acceptors. IDCP was the most efficient promoter in coupling of perbenzylated ethylthio-α-D-mannopyranosides (1 and 2), giving α-Dmannosyl disaccharides preferentially, whereas inactive in coupling of 4,6-O-benzylidene derivatives 3 and 4. MeOTf and DMTST promoted coupling of 4,6-O-benzylidene derivatives 3 and 4, but P-D-mannopyranosyl disaccharides were formed preferentially. Coupling reaction was retarded as solvent polarity decreased.

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