Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside disodium salts, related to heparin biosynthesis
Articolo
Data di Pubblicazione:
1996
Citazione:
Synthesis of the disaccharides methyl 4-O-(2'/3'-O-sulfo-beta-D-glucopyranosyluronic acid)-2-amino-2-deoxy-alpha-D-glucopyranoside disodium salts, related to heparin biosynthesis / L. Cipolla, F. Nicotra, L. Lay, U. Lindahl, L. Panza, G. Russo. - In: GLYCOCONJUGATE JOURNAL. - ISSN 0282-0080. - 13:6(1996), pp. 995-1003.
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Carbohydrates; Heparin biosynthesis; Sulfated disaccharides; Synthesis
Elenco autori:
L. Cipolla, F. Nicotra, L. Lay, U. Lindahl, L. Panza, G. Russo
Link alla scheda completa: