title: Stereoselective synthesis of 2-C-acetonyl-2-deoxy-D-galactosides using 1,2-cyclopropaneacetylated sugar as novel glycosyl donor.
abstract: 1,2-Cyclopropaneacetylated sugar is an effective glycosyl donor, which reacted with various glycosyl acceptors including monosaccharides, amino acids and other alcohols in the presence of BF(3)*OEt(2) or TMSOTf. The glycosylation is stereoselective in favor of beta-anomeric products with BF(3)*OEt(2) as catalyst, whereas TMSOTf-catalyzed glycosylation prefers the alpha-anomeric products. 2-C-Acetonyl-2-deoxy-D-galactosides were obtained in good yields.
authors.affiliation: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Tian
authors.forename: Liyan
authors.initials: L
authors.lastname: Xu
authors.forename: Xiaofeng
authors.initials: X
authors.lastname: Ma
authors.forename: Wei
authors.initials: W
authors.lastname: Zou
authors.forename: Huawu
authors.initials: H
authors.lastname: Shao
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D005697:Galactosides