Stereoselective synthesis of 2-C-acetonyl-2-deoxy-D-galactosides using 1,2-cyclopropaneacetylated sugar as novel glycosyl donor.
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.
Tian
Qiang
Q
Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
Xu
Liyan
L
Ma
Xiaofeng
X
Zou
Wei
W
Shao
Huawu
H
D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D002241:Carbohydrates; D005697:Galactosides