191216-63-4Relevant academic research and scientific papers
Intramolecular glycosylation of prearranged glycosides part 5. α-(1→4)-Selective glucosylation of glucosides and glucosamines
Ziegler, Thomas,Ritter, Axel,Huerttlen, Juergen
, p. 3715 - 3718 (2007/10/03)
The intramolecular (1→4) glucosylation of partially protected alkyl glucosides and glucosamines with phenyl 1-thioglucoside that is preconnected via its position 2 by a succinyl spacer to positions 3 of the glucosyl acceptor affords the α-linked disaccharides. The anomeric selectivity depends on the stereochemistry of the donor-acceptor-interaction and is not governed by neighboring group participation. In contrast, connecting the glucosyl donor by the succinyl bridge to position 6 of the glucosamine acceptor results in an α/β-mixture of the corresponding disaccharides upon intramolecular glycosylation.
