The synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside 3 and 4 as disodium salts is described. Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside 6 was converted to trichloroacetimidate 20. Glycosylation of 20 with 5 promoted by BF3 . OEt(2) gave disaccharide 21. Deacetylation of 21 followed by monoacetylation of the resultant diol 22 afforded the two monoacetylated disaccharides 23 and 24. Sulfation and deprotection of each disaccharide gave the desired sulfated compounds 3 and 4.
Cipolla, L., Nicotra, F., Lay, L., Lindahl, U., Panza, L., Russo, G. (1996). Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-β-D-glucopyranosyluronic acid)-2-amino-2-deoxy-α-D-glucopyranoside disodium salts, related to heparin biosynthesis. GLYCOCONJUGATE JOURNAL, 13(6), 995-1003 [10.1007/BF01053195].
Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-β-D-glucopyranosyluronic acid)-2-amino-2-deoxy-α-D-glucopyranoside disodium salts, related to heparin biosynthesis
CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO;
1996
Abstract
The synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside 3 and 4 as disodium salts is described. Allyl 4,6-O-benzylidene-alpha-D-glucopyranoside 6 was converted to trichloroacetimidate 20. Glycosylation of 20 with 5 promoted by BF3 . OEt(2) gave disaccharide 21. Deacetylation of 21 followed by monoacetylation of the resultant diol 22 afforded the two monoacetylated disaccharides 23 and 24. Sulfation and deprotection of each disaccharide gave the desired sulfated compounds 3 and 4.
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