Insertion of aD-glucosamine residue into the α-cyclodextrin skeleton; a model synthesis of ‘chimera cyclodextrins’
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 289-290
- https://doi.org/10.1039/c39910000289
Abstract
Efficient conversion of α-cyclodextrin peracetate 2 into icosa-O-acetylmaltohexaose 3 by acetolytic fission of one glycosidic linkage, a series of manipulations including coupling with a 2-azido-2-deoxy-D-glucopyranose derivative, recyclization and final work-up (catalytic hydrogenolysis etc.) gave a novel β-cyclodextrin analogue 10 containing a D-glucosamine residue as a monosaccharide component.Keywords
This publication has 10 references indexed in Scilit:
- Stereoselectivity of cycloglycosylation in mannooligose series depends on carbohydrate chain length: Syntheses of manno isomers of β- and γ- cyclodextrinsTetrahedron Letters, 1990
- First regiospecific synthesis of 6A,6C,6E-tri-O-methylyclomaltohexaoseJournal of the Chemical Society, Chemical Communications, 1989
- A new, stereoselective synthesis of methyl 1,2-trans-1-thioglycosidesTetrahedron Letters, 1987
- Total synthesis of cyclomaltooctaose and an isomer of cyclomaltohexaose, cyclo{→6)-[α-d-Glcp-(1→4)]5-α-d-Glcp-(1-}Carbohydrate Research, 1987
- Total synthesis of cyclomaltohexaoseCarbohydrate Research, 1987
- New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]Angewandte Chemie International Edition in English, 1986
- Synthesis of chemically modified cyclodextrinsTetrahedron, 1983
- Reductive Ring Openings of Carbohydrate Benzylidene Acetals Using Borane-Trimethylamine and Aluminium Chloride. Regioselectivity and Solvent DependanceJournal of Carbohydrate Chemistry, 1983
- Cyclodextrin catalysis as a model for enzyme actionAccounts of Chemical Research, 1982
- Über Einschlußverbindungen, XX. ORD‐Spektren und Konformation der Glucose‐Einheiten in CyclodextrinenEuropean Journal of Inorganic Chemistry, 1969