PMID: 3756957Aug 1, 1986Paper

Streptococcus pneumoniae type XIV polysaccharide: synthesis of a repeating branched tetrasaccharide with dioxa-type spacer-arms

Carbohydrate Research
P H Amvam-Zollo, P Sinaÿ

Abstract

beta-Glycosides of 2-acetamido-2-deoxy-D-glucopyranose were synthesised, using either 7-methoxycarbonyl-3,6-dioxa-1-heptanol or 8-azido-3,6-dioxa-1-octanol. Selective beta-lactosylation of 7-methoxycarbonyl-3,6-dioxaheptyl 2-acetamido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside with hepta-O-acetyl-lactosyl-trichloroacetimidate, followed by beta-galactosylation of the secondary hydroxyl group with O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)trichloroacetimida te, catalytic hydrogenolysis, and O-deacetylation, gave 7-methoxycarbonyl-3,6-dioxaheptyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-6-O-(4-O-beta-D- galactopyranosyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside. Selective beta-lactosylation of 8-azido-3,6-dioxaoctyl 2-acetamido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside with hepta-O-acetyl-lactosyl bromide in the presence of silver triflate, followed by condensation with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide in the presence of silver triflate, catalytic hydrogenolysis, and O-deacetylation, gave 8-azido-3,6-dioxaoctyl 2-acetamido-2-deoxy-4-O-beta-D-galactopyranosyl-6-O-(4-O-beta-D- galactopyranosyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside.

Citations

May 21, 2010·Beilstein Journal of Organic Chemistry·An WangFrance-Isabelle Auzanneau
Dec 16, 2000·Carbohydrate Research·A K SarkarJ D Esko
Jun 14, 2008·Carbohydrate Research·Jun-Ichi SakamotoKoji Matsuoka
Mar 7, 2006·Carbohydrate Research·Nicolas LaurentPaul Boullanger
Sep 27, 2018·Chemistry : a European Journal·Franziska ReiseThisbe K Lindhorst
Jan 11, 2019·Bioconjugate Chemistry·Diksha HaksarRoland J Pieters
Mar 7, 2007·Journal of the American Chemical Society·Nour Eddine FahmiSidney M Hecht
Jan 2, 2010·Carbohydrate Research·Verónica M MendozaCarola Gallo-Rodriguez

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