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
Jun 1, 1990·Antonie van Leeuwenhoek·J E van DamH Snippe
Aug 19, 2007·Glycoconjugate Journal·Yanli CuiYongmin Zhang
Mar 1, 1995·Carbohydrate Research·H PaulsenK Bock
Apr 9, 2002·Bioorganic & Medicinal Chemistry·Seiichiro OgawaYoshiyuki Suzuki
Nov 5, 1998·Bioorganic & Medicinal Chemistry·J NiggemannJ F Vliegenthart
Sep 11, 1999·Bioorganic & Medicinal Chemistry·J LiP G Wang
Mar 20, 2010·Organic & Biomolecular Chemistry·Jeroen van AmeijdeRob M J Liskamp
Jan 8, 2004·Chemical & Pharmaceutical Bulletin·Akiko IkutaToshiko Tanimoto
May 21, 2010·Beilstein Journal of Organic Chemistry·An WangFrance-Isabelle Auzanneau
Dec 16, 2000·Carbohydrate Research·A K SarkarJ D Esko
Apr 24, 1991·Carbohydrate Research·A M van SteijnJ F Vliegenthart
Dec 13, 1996·Carbohydrate Research·W ZouH J Jennings
Oct 12, 2012·Organic & Biomolecular Chemistry·Verónica E ManzanoOscar Varela
Oct 14, 1991·Carbohydrate Research·S RioJ C Jacquinet
Jun 14, 2008·Carbohydrate Research·Jun-Ichi SakamotoKoji Matsuoka
Dec 27, 1995·Carbohydrate Research·A K Sarkar, J D Esko
Jun 14, 2002·Carbohydrate Research·Keith ClinchDamian P Wright
May 3, 2006·Carbohydrate Research·Bart Ruttens, Pavol Kovác
Jul 19, 1993·Carbohydrate Research·B DeanT Toyokuni
Apr 11, 2015·The Journal of Organic Chemistry·Deng KuirFrance-Isabelle Auzanneau
Mar 7, 2006·Carbohydrate Research·Nicolas LaurentPaul Boullanger
Sep 27, 2018·Chemistry : a European Journal·Franziska ReiseThisbe K Lindhorst
Aug 9, 2006·The Journal of Biological Chemistry·Raman Deep SinghRichard E Pagano
Jul 5, 2019·Carbohydrate Research·Gustavo A KashiwagiCarola Gallo-Rodriguez
Jun 4, 1992·Carbohydrate Research·T SugawaraY Ito
Sep 19, 1990·Carbohydrate Research·V PozsgayH J Jennings
May 16, 2006·Carbohydrate Research·Andrew J RossAndrei V Nikolaev
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