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- W2017508366 endingPage "1382" @default.
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- W2017508366 abstract "The development of an efficient method for the stereoselective synthesis of alpha-D-(2-->1)-linked ketoside oligomers is described. The method is based on an iterative protocol composed of two key steps: a) the coupling of a thiazolylketosyl phosphite donor with an hydroxymethylketoside acceptor; and b) the introduction of the hydroxy-methyl group at the anomeric carbon atom of the resulting oligomer. To highlight its efficiency, the protocol was used in the assembly of D-galacto-2-heptulopyranose-containing oligoketosides through alpha-(2-->1) linkages up to the pentameric stage. The yield of the isolated oligomers ranged from 48 % in the first cycle to 29% in the fourth cycle. Having employed a pentenyl-substituted hydroxymethylketoside acceptor in the first cycle, all the derived oligomers contained the pentenyl group at their reducing end. This group was exploited to transform the linear oligomers into cyclic products through intramolecular glycosidation. The major product derived from the linear trisaccharide was confirmed by X-ray crystallography to be the cyclotris-(2-->1)-(alpha-D-galacto-2-heptulopyranosyl). The structure of this compound was essentially that of a [9]crown-3 ether bearing three galactopyranose rings spiroanellated in a propellerlike fashion. This arrangement of carbohydrate units linked to the crown ether created a densely alkoxylated cavity suitable for the encapsulation of alkali-metal cations (Li, Na, K, Ca, Mg)." @default.
- W2017508366 created "2016-06-24" @default.
- W2017508366 creator A5010979417 @default.
- W2017508366 creator A5025961287 @default.
- W2017508366 creator A5040406233 @default.
- W2017508366 creator A5080265681 @default.
- W2017508366 date "2001-04-01" @default.
- W2017508366 modified "2023-10-18" @default.
- W2017508366 title "Chemical Synthesis of Linear and Cyclic Unnatural Oligosaccharides by Iterative Glycosidation of Ketoses" @default.
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- W2017508366 doi "https://doi.org/10.1002/1521-3765(20010401)7:7<1371::aid-chem1371>3.0.co;2-j" @default.