Synthesis of Lactose-Based S-Linked Sialylmimetics of α(2,3)-Sialosides
- 21 October 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (23), 4365-4368
- https://doi.org/10.1021/ol035733d
Abstract
A new approach toward the synthesis of lactose-based S-linked sialylmimetics of a(2,3)-linked sialosides is described. These compounds, represented by the general structure 3, were prepared from methyl ߭d-lactoside in 11 steps. It was found that the choice of protecting group was crucial to allow the efficient introduction of sulfur at the 3-position of the galactose ring.Office of the Snr Dep Vice Chancellor, Institute for GlycomicsNo Full TexKeywords
This publication has 17 references indexed in Scilit:
- Chemical Diversity in the Sialic Acids and Related α-Keto Acids: An Evolutionary PerspectiveChemical Reviews, 2002
- Chemical GlycobiologyScience, 2001
- Glycosphingolipid Binding Specificities of Rotavirus: Identification of a Sialic Acid-Binding EpitopeJournal of Virology, 2001
- Receptor Binding and Membrane Fusion in Virus Entry: The Influenza HemagglutininAnnual Review of Biochemistry, 2000
- Carbohydrate Mimetics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological RecognitionAngewandte Chemie-International Edition, 1999
- Selectin−Carbohydrate Interactions: From Natural Ligands to Designed MimicsChemical Reviews, 1998
- A one-step synthesis of 6-S-acetyl-6-deoxy-1,2:3,4-di-O-isopropylidene-6-thio-α-d-galactopyranoseCarbohydrate Research, 1990
- Stereoselective synthesis of sialyl-lactotetraosylceramide and sialylneolactotetraosylceramideCarbohydrate Research, 1990
- 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugarsThe Journal of Organic Chemistry, 1988
- Regioselective manipulation of hydroxyl groups via organotin derivativesTetrahedron, 1985