An Efficient Synthesis of Cyclodextrin-Based Carbohydrate Cluster Compounds
- 24 March 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (8) , 1113-1116
- https://doi.org/10.1021/ol005668x
Abstract
The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-β-d-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6-diallyl-β-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of β-cyclodextrinnot to mention (3) both the primary and secondary faces, simultaneouslyin yields of up to 70%.Keywords
This publication has 19 references indexed in Scilit:
- Interaction of Sugar and Anion in Water via Hydrogen Bonding: Chain-Length Dependent Agglutination of Oligosaccharide Clusters Induced by Multivalent Anion BindingJournal of the American Chemical Society, 1999
- On the Meaning of Affinity: Cluster Glycoside Effects and Concanavalin AJournal of the American Chemical Society, 1999
- Organically Templated Mixed-Valent TiIII/TiIV Phosphate with an Octahedral- Tetrahedral Open FrameworkAngewandte Chemie International Edition in English, 1999
- Ternary Complexation Involving Protein. Molecular Transport to Saccharide-Binding Proteins Using Macrocyclic Saccharide Cluster as Specific TransporterJournal of the American Chemical Society, 1998
- Solution-to-Surface Molecular-Delivery System Using a Macrocyclic Sugar Cluster. Sugar-Directed Adsorption of Guests in Water on Polar Solid SurfacesJournal of the American Chemical Society, 1997
- Calixsugars:† Preparation of Upper Rim O-Ketopyranosyl Calix[4]arenesThe Journal of Organic Chemistry, 1996
- The Synthesis of Functionalized Cyclodextrins As Scaffolds and Templates for Molecular Diversity, Catalysis, and Inclusion PhenomenaThe Journal of Organic Chemistry, 1995
- Cyclodextrins as Building Blocks for Supramolecular Structures and Functional UnitsAngewandte Chemie International Edition in English, 1994
- Recognition ability and cytotoxicity of some oligosaccharidylsubstituted β‐cyclodextrinsBiology of the Cell, 1994
- New β-cyclodextrin derivatives possessing biologically active saccharide antennaeSupramolecular Chemistry, 1993