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One-Pot Synthesis of Asymmetrically Difunctionalized Oligomaltosides by Cyclodextrin Ring Opening

Overview
Journal ChemistryOpen
Specialty Chemistry
Date 2021 Apr 28
PMID 33908706
Citations 2
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Abstract

The synthesis of pure difunctionalized hexa-, hepta- and octamaltosides was performed by one-pot chemical reaction from perbenzoylated cyclodextrin. Oligomaltosides with azide, propargyl or allyl on reducing end and an unprotected hydroxyl group on non-reducing end were obtained from perbenzoylated α-, β- and γ-cyclodextrin with 12 to 48 % yields.

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One-Pot Synthesis of Asymmetrically Difunctionalized Oligomaltosides by Cyclodextrin Ring Opening.

Pelingre M, Smadhi M, Bil A, Bonnet V, Kovensky J ChemistryOpen. 2021; 10(4):493-496.

PMID: 33908706 PMC: 8080284. DOI: 10.1002/open.202100079.

References
1.
Nokami T, Shibuya A, Saigusa Y, Manabe S, Ito Y, Yoshida J . Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation. Beilstein J Org Chem. 2012; 8:456-60. PMC: 3326625. DOI: 10.3762/bjoc.8.52. View

2.
Bosch A, Mischnick P . Bifunctional building blocks for glyco-architectures by TiCl4 -promoted ring opening of cyclodextrin derivatives. Biomacromolecules. 2007; 8(7):2311-20. DOI: 10.1021/bm0702612. View

3.
de Medeiros Modolon S, Otsuka I, Fort S, Minatti E, Borsali R, Halila S . Sweet block copolymer nanoparticles: preparation and self-assembly of fully oligosaccharide-based amphiphile. Biomacromolecules. 2012; 13(4):1129-35. DOI: 10.1021/bm3000138. View

4.
Crini G . Review: a history of cyclodextrins. Chem Rev. 2014; 114(21):10940-75. DOI: 10.1021/cr500081p. View

5.
Farkas E, JANOSSY L, Harangi J, Kandra L, Liptak A . Synthesis of chromogenic substrates of alpha-amylases on a cyclodextrin basis. Carbohydr Res. 1997; 303(4):407-15. DOI: 10.1016/s0008-6215(97)00187-0. View