Synthesis of Glycosyl Azides by the Addition of Phenylselenenyl Azide to Glycals
- 1 December 1994
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 13 (8) , 1135-1143
- https://doi.org/10.1080/07328309408011855
Abstract
The addition of phenylselenenyl azide to glycals is carried out under conditions that give 2-deoxy-2-phenylselenoglycosyl azides. This regiochemistry is opposite to that obtained under free-radical conditions, which are known to produce 2-azido-2-deoxyselenoglycosides. The addition reaction is carried out with phenylselenenyl chloride and sodium azide in dimethylformamide, and is stereoselective for trans addition. Tri-O-benzyl-d-glucal and di-O-benzyl-l-rhamnal each gave two addition products, in which the phenylselenyl and azido groups were either trans diaxial or trans diequatorial. Tri-O-benzyl-d-galactal gave only the trans diaxial addition product.Keywords
This publication has 19 references indexed in Scilit:
- Azido-phenylselenylation of protected glycalsTetrahedron Letters, 1993
- Synthesis of phenyl 2-azido-2-deoxy-1-selenoglycosides from glycalsThe Journal of Organic Chemistry, 1993
- Synthesis, Structure and Reactions of Glycosyl AzidesJournal of Carbohydrate Chemistry, 1993
- A stereoselective route from glycals to asparagine-linked N-protected glycopeptidesThe Journal of Organic Chemistry, 1992
- Azides: their preparation and synthetic usesChemical Reviews, 1988
- Studies on N-Glycopeptides. II. Separation of α- and β-Amide of N-(l-Aspartyl)-β-d-glucopyranosylamine Obtained via N-(Benzyloxycarbonyl)-l-aspartic AnhydrideBulletin of the Chemical Society of Japan, 1984
- Advances in Selective Chemical Syntheses of Complex OligosaccharidesAngewandte Chemie International Edition in English, 1982
- Syntheses of cellobiosyl, maltosyl, and lactosyl derivatives of asparagineCarbohydrate Research, 1972
- The Synthesis of a Di-N-acetylchitobiose Asparagine Derivative, 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-1-N-(4-l-aspartyl)-2-deoxy-β-d-glucopyranosylaminePublished by Elsevier ,1970
- The Synthesis of a Glucosamine—Asparagine Compound. Benzyl N2-Carbobenzyloxy-N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-asparaginate1The Journal of Organic Chemistry, 1963