Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide
- 27 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (6) , 1638-1639
- https://doi.org/10.1021/ja039374t
Abstract
A convergent strategy for the synthesis of β-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido−alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and β-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.Keywords
This publication has 29 references indexed in Scilit:
- Selective Tetrafunctionalisation of α‐Cyclodextrin using the Supertrityl Protecting Group − Synthesis of the First C2‐Symmetric Tetraphosphane Based on a Cavitand (α‐TEPHOS)European Journal of Organic Chemistry, 2003
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie International Edition in English, 2002
- Cyclodextrin-Based Molecular MachinesAccounts of Chemical Research, 2001
- Dehydrative Glycosylation with Activated Diphenyl Sulfonium Reagents. Scope, Mode of C(1)-Hemiacetal Activation, and Detection of Reactive Glycosyl IntermediatesJournal of the American Chemical Society, 2000
- Layered molecular optoelectronic assembliesJournal of Materials Chemistry, 1998
- Glycoside Synthesis with Anomeric 1-N-Glycobiosyl-1,2,3-triazoles1Journal of Carbohydrate Chemistry, 1996
- Cyclic dimerization of 1,2-unsaturated maltotriose derivatives with iodinium addition; one-pot preparation of a fully methylated 2 A ,2 D -dideoxy-2 A ,2 D -diiodocyclohexasaccharideJournal of the Chemical Society, Chemical Communications, 1993
- Inclusion Complex of 8-Anilinonaphthalene-1-sulfonate with β-CyclodextrinJournal of Pharmaceutical Sciences, 1991
- Role of specific solvation in the fluorescence sensitivity of 1,8-ANS to waterThe Journal of Physical Chemistry, 1989
- 1.3‐Dipolare Cycloadditionen, XXIII. Einige Beobachtungen zur Addition organischer Azide an CC‐DreifachbindungenEuropean Journal of Inorganic Chemistry, 1965