โ Scribed by Marianne Nilsson; Carl-Magnus Svahn; Jacob Westman
No coin nor oath required. For personal study only.
The methyl glycoside of a tetrasaccharide isolated from heparin, methyl 0-(a-t_-idopyranosyluronic acidM1 + 4)-O-(2-acetamido-2-deoxy-a-o-glucopyranosyl)-(1 -+ 4)-o-(p-oglucopyranosyluronic acid)-(1 -+ 3)-0-P-o-gafactopyranoside disodium salt and a trisaccharide derivative thereof, methyl 0-(a-L-idopyranosyluronic acid&(1 -+ 4)-O-(2-acetamido-2-deoxy+o-giucopyra-nosy&(1 + 4)-0-P-o-glucopyranosyluronic
acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri-and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.
๐ SIMILAR VOLUMES
Methyl 4-(3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-alpha-D- mannopyranoside was acetylated, and the fully protected methyl glycoside was treated with dichloromethyl methyl ether-ZnCl2 (DCMME-ZnCl2) reagent to give 3-O-acetyl-4-(2,4-di-O-acetyl-3- deoxy-L-glycero-tetronamido)-4,6-dideoxy
Syntheses of the propyl glycosides (1-3) of beta-D-Galp-(1----4)-beta-D-GlcpNAc, beta-D-Glcp-(1----6)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc, and beta-D-Galp-(1----4)-beta-D-Glcp-(1----6)-[beta-D-Galp-(1----)]-beta-D- GlcpNAc, respectively, are reported. Reaction of allyl 2-acetamido-3-O-benzyl-2-deo