Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: 2,3-Unsaturated- C -aryl glycopyranosides are important intermediates in the synthesis of medicinally important C - Daryl glycosides and likely involves the formation of an oxocarbenium ion intermediate via indium(III) Lewis acid-assisted ionization of the glycal C.3 acetate.
29 citations
TL;DR: In this paper, the Ireland-Claisen rearrangement of the allyl ester 5 and a stereoselective epoxidation of the furanoid glycal 12 with 2,2-dimethyldioxirane were used to synthesize the squalestatins and zaragozic acids.
29 citations
TL;DR: In this article, a quaternary ammonium tribromides as bromine donors are used as donors for the α-1,2-trans dibromo adducts.
Abstract: Addition of bromine to glycals using quaternary ammonium tribromides as bromine donors is realized with higher stereoselectivities (α-1,2-trans configurated products) compared to bromination with molecular bromine. The reaction is neither sensitive to the solvent nor to the nature of the protecting groups (acetyl, benzoyl, benzyl) of the glycals and very slightly affected by the orientation of the substituents of the different glycals. Some of the α-1,2-trans dibromo adducts have been isolated in 60-75% yields and transformed into the corresponding α-1,2-trans-2-bromo-2-deoxyglycopyranosyl fluorides
28 citations
28 citations
TL;DR: The addition of a sulphonyl radical to the external double bond of an allyl glycal generates a pro-chiral carbon radical which adds to the glycal double bond with a high diastereoselectivity as discussed by the authors.
28 citations