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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 11
BKCSDE 19(11)
November 20, 1998 

Syntheses of Mannosidec Disaccharides from Derivatives of Ethylthio α-D-Mannopyranoside
Mikyung Yun, Youngsook Shin, Shinsook Yoon, Keun Ho Chun, Jeong E. Nam Shin
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.
1239 - 1244
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