title: Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation.
abstract: The formation of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose was observed in the gold(I)-catalyzed glycosidation of peracetyl glucopyranosyl ortho-hexynylbenzoate; experiments with substrates bearing deuterium labeled 2-O-acetyl or 4-O-acetyl groups indicated that the orthoacetate was derived from the 4-O-acetyl group, which provided a direct evidence for the remote participation of the 4-O-acyl group in glycosylation.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Yuyong
authors.initials: Y
authors.lastname: Ma
authors.forename: Gaoyan
authors.initials: G
authors.lastname: Lian
authors.forename: Yao
authors.initials: Y
authors.lastname: Li
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D005960:Glucosides