Glycosylating reagent for the synthesis of linear and other .alp

Details Glycosylating reagent for the synthesis of linear and other .alp Glycosylating reagent for the synthesis of linear and other .alp

1991-07-16

1995-08-01

Redding, David A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 181, 536123, 536 62, C07G 300, C07H 1500, C07H 1524

Patent

active

054381240

ABSTRACT:
A novel, efficient glycosylating reagent, R 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-.beta. -L-fucopyranoside wherein R is a lower alkyl or lower alkenyl of 1 to 8 carbons such as methyl or pentenyl, is described. This novel reagent provides for the facile synthesis of linear and other .alpha.-L-fucosyl oligosaccharides. In addition, a method for the preparation of 2'-O-.alpha.-L-fucopyranosyl-lactose, which comprises reacting the abovementioned glycosylating reagent with solvated 4-O-(6-O-acetyl-3,4-O-isopropylidene-.beta.-D-galactopyranosyl)-2,3,5,6-di -O-isopropylidene-D-glucose, dimethyl acetal, a tetrabutylammonium halide and a catalyst and then de-O-acetylating the resulting reaction product with sodium methoxide methanol, is also disclosed.

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Hakomori, S. et al., J. Biol. Chem., 259:4672-4680 (1984).
Fukushi, Y. et al., J. Biol. Chem. 259:4681-4685 (1984).

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