G. Lemanski et T. Ziegler, Prearranged glycosides Part 13 - Intramolecular mannosylations of glucosamine, galactose, mannose, and rhamnose derivatives via prearranged glycosides, HELV CHIM A, 83(10), 2000, pp. 2676-2697
A series of prearranged glycosides 4, 9, 14, 16, 22, 28, 33, 41, and 46, ha
ving a benzyl-protected 1-thiomannosyl donor linked through its position 6
via malonate and succinate tethers to various positions of glucosamine, gal
actose, mannose, and rhamnose accepters, were prepared and cyclized to the
corresponding disaccharides. The configuration at the anomeric center of th
e products strongly depended on the position of the tt ther in the acceptor
part and could be predicted from the calculated thermodynamic stability of
the products. No strong dependence of the diastereoselectivity of the intr
amolecular glycosylations on the activation conditions and the solvent was
observed.