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.
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.OEt2 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
L
Dipartimento di Chimica Organica e Industriale, Università di Milano, Italy.
Nicotra
F
F
Lay
L
L
Lindahl
U
U
Panza
L
L
Russo
G
G
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004187:Disaccharides / Q000138:chemical synthesis*; D006493:Heparin / Q000096:biosynthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction
D004187:Disaccharides; C104893:methyl-4-O-(2'-O-sulfoglucopyranosyluronic acid)-2-amino-2-deoxyglucopyranoside; C104894:methyl-4-O-(3'-O-sulfoglucopyranosyluronic acid)-2-amino-2-deoxyglucopyranoside; D006493:Heparin