Novel 4-thiogalactofuranosyl-containing disaccharides with nitrogen in the interglycosidic linkage.
The syntheses of three novel disaccharides containing a 4-thiogalactofuranosyl residue as the non-reducing unit and a nitrogen in the interglycosidic linkage are described. Acid-catalyzed condensation reactions of 4-thio-alpha/beta-D-galactofuranose with either methyl 3-amino-3-deoxy-alpha-D-mannopyranoside, methyl 2-amino-2-deoxy-alpha-D-mannopyranoside, or methyl 2-acetamido-6-amino-2,6-dideoxy-beta-D-glucopyranoside gave methyl 3-amino-3-deoxy-3-N-(4-thio-alpha/beta-D-galactofuranosyl)-alpha-D-manno pyranoside, methyl 2-amino-2-deoxy-2-N-(4-thio-alpha/beta-D-galactofuranosyl)-alpha-D-manno pyranoside, or methyl 2-acetamido-6-amino-2,6-dideoxy-6-N-(4-thio-alpha/beta-D-galactofuranosy l)-beta-D-glucopyranoside.
Randell
K D
KD
Department of Chemistry, Simon Fraser University, Burnaby BC, Canada.
Johnston
B D
BD
Pinto
B M
BM
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D013862:Thiogalactosides / Q000737:chemistry*
D004187:Disaccharides; D006027:Glycosides; D013862:Thiogalactosides; D013455:Sulfur; D009584:Nitrogen