Synthetic Studies on Sialoglycoconjugates 36: α-Selective Glycoside Synthesis of N-Acetylneuraminic Acid with the Secondary Hydroxyl Group in D-Glucofyranose, 2-Acetamido-2-deoxy-D-glucopyranose and D-Galactopyranose Derivatives
- 1 April 1992
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 11 (3) , 333-341
- https://doi.org/10.1080/07328309208017997
Abstract
Coupling of the secondary hydroxyl group in the 6-O-benzoyl derivatives 3, 5 and 8, prepared from 2-(trimethylsilyl)ethyl β-D-glucopyranoside (2), 2-acetamido-2-deoxy-β-D-glucopyranoside (4), and 2-acetamido-2-deoxy-β-D-galactopyranoside (6), with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate (1) as the glycosyl donor in acetonitrile in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) as a glycosyl promoter, exclusively gave the cx-glycosides at C-2 in 3, at C-3 in 5 and 8, respectively.Keywords
This publication has 11 references indexed in Scilit:
- Glycosidation of sialic acidTetrahedron, 1990
- Highly stereoselective glycosylation of sialic acid aided by stereocontrolling auxiliariesTetrahedron, 1990
- Iodonium promoted reactions of disarmed thioglycosidesTetrahedron Letters, 1990
- Synthetic Studies on Sialoglycoconjugates 16: α-Predominant Glycoside Synthesis of N-Acetylneuraminic Acid With the Primary Hydroxyl Group in Carbohydrates Using Dimethyl(Methylthio)Sulfonium Triflate as a Glycosyl PromoterJournal of Carbohydrate Chemistry, 1990
- Synthetic Studies on Sialoglycoconjugates. 5: A Facile, Regio and Stereoselective Synthesis of Ganglioside GM4and Its Position Isomer1Journal of Carbohydrate Chemistry, 1989
- Synthesis and immunoadjuvant activity of the conjugates of 1-thio-N-acetyl-muramoyl dipeptide with lipid A subunit analogs.Agricultural and Biological Chemistry, 1989
- A facile regio- and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acidCarbohydrate Research, 1988
- 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugarsThe Journal of Organic Chemistry, 1988
- An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillaryTetrahedron Letters, 1987
- A novel promoter for the efficient construction of 1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl donorsCarbohydrate Research, 1986