Cyclic Disaccharide Formation Enforced by a Ring Contraction: 2,3-Dideoxy Pyranoside Glycoside Donor to a Furanoside Macrocycle

Sarkar, B and Pramanik, T and Jayaraman, N (2022) Cyclic Disaccharide Formation Enforced by a Ring Contraction: 2,3-Dideoxy Pyranoside Glycoside Donor to a Furanoside Macrocycle. In: Journal of Organic Chemistry .

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Abstract

The synthesis of a disaccharide macrocycle through 2,3-dideoxy glucopyranosyl monosaccharide is reported. 2,3-Dideoxy-erythro-hexopyranosyl thioglycoside possessing a free hydroxy functionality at the C-4 carbon is prepared, and cycloglycosylation is conducted. In the event, the cycloglycosylation occurs with a ring contraction of the monosaccharide moiety and affords the cyclic furanoside disaccharide. Solution-phase and single-crystal X-ray diffraction structural characterizations permit the features of the macrocycle to be uncovered. The solubilization and encapsulation properties of the macrocycle are studied in aqueous solutions with 1-aminoadamantane. © 2022 American Chemical Society.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	19 Jan 2023 10:11
Last Modified:	19 Jan 2023 10:11
URI:	https://eprints.iisc.ac.in/id/eprint/79213

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