Hp. Wessel et al., SELECTIVELY DEOXYGENATED DERIVATIVES OF BETA-MALTOSYL-(1-]4)-TREHALOSE AS BIOLOGICAL PROBES, Journal of carbohydrate chemistry, 15(5), 1996, pp. 523-548
The four derivatives of beta-maltosyl-(1 --> 4)-trehalose have been sy
nthesized, which are monodeoxygenated at the site of one of the primar
y hydroxyl groups. The tetrasaccharides were constructed in [2+2] bloc
k syntheses. Thus, 6'''-deoxy-beta-maltosyl-(1 --> 4)-trehalose was pr
epared by selective iodination of allyl 2,3,6,2',3'-penta-O-acetyl-bet
a-maltoside (3) followed by catalytic hydrogenolysis and coupling with
-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2',3',6'-tri-O-ben
zyl-alpha-D-glucopyranoside (9), and 6 ''-deoxy-beta-maltosyl-(1 --> 4
)-trehalose by selective iodination of allyl 4',6'-O-isopropylidene-be
ta-maltoside (14), coupling with 9, and one-step hydrogenolysis at the
tetrasaccharide level. For the synthesis of 6'-deoxy-beta-maltosyl-(1
--> 4)-trehalose, the diol -O-benzyl-4,6-O-benzylidene-alpha-D-glucop
yranosyl 2',3'-di-O-benzyl-alpha-D-glucopyranoside (22) was selectivel
y iodinated and glycosylated with acetobromomaltose followed by cataly
tic hydrogenolysis. The 6-deoxy-beta-maltosyl-(1 --> 4)-trehalose was
obtained upon selective iodination of a tetrasaccharide diol.