New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Stereoselective α- and β-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group
- 1 May 1994
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 67 (5) , 1359-1366
- https://doi.org/10.1246/bcsj.67.1359
Abstract
The reactions of mannopyranosyl dimethylphosphinothioates and alcohols using silver perchlorate as an activator in the presence of molecular sieves 4A in benzene at room temperature gave the 1,2-trans-α-mannopyranosides in good yields. On the other hand, 1,2-cis-β-mannopyranosides could be obtained from the dimethylphosphinothioates by the combined use of iodine and 5 mol% triphenylmethyl perchlorate as an activating system. The syntheses of the derivatives of αMan(1→6)[αMan(1→3)]Man and βMan(1→4)GlcNAc units of glycoproteins by these methods are described.This publication has 19 references indexed in Scilit:
- Stereocontrolled synthesis of disaccharides via the temporary silicon connectionJournal of the American Chemical Society, 1992
- Synthesis of .beta.-mannopyranosides by intramolecular aglycon deliveryJournal of the American Chemical Society, 1991
- Cp2ZrCl2AgBF4 in Benzene: A new reagent system for rapid and highly selective α-mannoside synthesis from tetra-O-benzyl-d-mannosyl fluorideTetrahedron Letters, 1989
- Synthesis of a branched mannohexaoside, a part structure of a high-mannose-type glycan of a glycoproteinCarbohydrate Research, 1985
- Substituent effects on carbohydrate coupling reactions promoted by insoluble silver saltsTetrahedron, 1984
- Retention of the anomeric configuration in the imidate procedure: synthesis of disaccharides containing α-l-rhamnopyranosyl and α-d-mannopyranosyl groupsCarbohydrate Research, 1982
- Synthesis of a branched d-mannopentaoside and a branched d-mannohexaoside: Models of the inner core of cell-wall glycoproteins of Saccharomyces cerevisiaeCarbohydrate Research, 1981
- Phosphinyl- and Phosphinothioylamino Acids and Peptides. V. Preparation of Dimethylphosphinothioylamino Acids and Solid Phase Peptide SynthesisBulletin of the Chemical Society of Japan, 1979
- Preparation of 2,3,4,6-Tetra-O-benzyl-d-mannoseBulletin of the Chemical Society of Japan, 1976
- Synthesis and methanolysis of 2,3,4-tri-O-benzyl-α-l- rhamnopyranosyl bromideCarbohydrate Research, 1975