Thioglycosides Protected as Trans-2,3-Cyclic Carbonates in Chemoselective Glycosylations
- 28 November 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (26) , 4201-4203
- https://doi.org/10.1021/ol016869j
Abstract
Thioglycosides protected as trans-2,3-cyclic carbonates have significantly lower anomeric reactivities than fully acylated and N-acyl-protected thioglycosides and can be used as acceptors in chemoselective glycosylations with a wide range of thioglycosyl donors. The resulting thioglycosides can be further activated to give 1,2-cis-linked glycosides.Keywords
This publication has 19 references indexed in Scilit:
- Oxazolidinone Protected 2-Amino-2-deoxy-d-glucose Derivatives as Versatile Intermediates in Stereoselective Oligosaccharide Synthesis and the Formation of α-Linked GlycosidesJournal of the American Chemical Society, 2001
- Programmable One-Pot Oligosaccharide SynthesisJournal of the American Chemical Society, 1999
- Tuning glycoside reactivity: New tool for efficient oligosaccharide synthesisJournal of the Chemical Society, Perkin Transactions 1, 1998
- Direct Formation of β-Mannopyranosides and Other Hindered Glycosides from ThioglycosidesJournal of the American Chemical Society, 1998
- Solvent and Other Effects on the Stereoselectivity of Thioglycoside GlycosidationsSynlett, 1997
- Preparation, structure, derivatisation and NMR data of cyclohexane-1,2-diacetal protected carbohydratesJournal of the Chemical Society, Perkin Transactions 1, 1997
- Synthesis of Disaccharides by Selective Metallocene Promoted Activation of Glycosyl FluoridesSynlett, 1996
- Stereoselective α-Sialylation with Sialyl Xanthate and Phenylsulfenyl Triflate as a PromotorThe Journal of Organic Chemistry, 1996
- n-Pentenyl Glycosides in Organic Chemistry: A Contemporary Example of SerendipitySynlett, 1992
- On the controlled oxidative coupling of glycals: a new strategy for the rapid assembly of oligosaccharidesJournal of the American Chemical Society, 1989