Solvent-Dependent, Kinetically Controlled Stereoselective Synthesis of 3- and 4-Thioglycosides
- 28 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (17), 6952-6955
- https://doi.org/10.1021/jo050650r
Abstract
Facile approaches to prepare 3- and 4-thioglycosides of the galacto, gulo, and gluco type from the parent triflates are presented. The dependencies of the solvent and the protecting group pattern, as well as the configuration of the neighboring and leaving groups, have been studied for these reactions. The results clearly show that the efficient stereoselective synthesis of methyl 3-thio-galactoside depends highly on the solvent and the nucleophile concentration.Keywords
This publication has 9 references indexed in Scilit:
- A Tandem Epoxidation/Stereoselective Intramolecular [4+3] Cycloaddition Reaction Involving Nitrogen‐Stabilized Oxyallyl Cations Derived from Chiral AllenamidesAngewandte Chemie-International Edition, 2004
- Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-SialosidesOrganic Letters, 2003
- Chemoenzymatic Syntheses of Linear and Branched Hemithiomaltodextrins as Potential Inhibitors for Starch-Debranching EnzymesChemistry – A European Journal, 2002
- Synthesis of α-GalNAc Thioconjugates from an α-GalNAc MercaptanThe Journal of Organic Chemistry, 2002
- Thiooligosaccharides as Tools for Structural BiologyChemBioChem, 2001
- Chemoselective Elaboration of O-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAcJournal of the American Chemical Society, 2001
- Novel features of acceptor recognition by β-(1→4)-galactosyltransferaseCarbohydrate Research, 1998
- Utilization of Sugars in Organic Synthesis. Part XXXIII. Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring: Formation of cis-Arranged Cyclic Thiolcarbonates.CHEMICAL & PHARMACEUTICAL BULLETIN, 1997
- Synthesis of a thio-linked analogue of sialyl Lewis XTetrahedron Letters, 1996