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: Under basic conditions, phenyl 1, 2-dithio-α-d-mannopyranoside forms a glycal-1,2-episulfide, which undergoes controlled oligomerization to afford a family of thio-oligo-β-D-mannOPyranosides, which might have application as mimics of natural structures such as viral high-mannose glycoproteins or ManLAM.
10 citations
TL;DR: In this article, the reaction of 3-hydroxy free glycals with O- or N-nucleophiles under Mitsunobu reaction conditions proceeded to produce 2,3-unsaturated glycosides in good to high yield and moderate stereoselectivity.
10 citations
TL;DR: In this paper, Nitrosyl tetrafluoroborate (NOBF4) has been successfully applied as an efficient organocatalyst for the preparation of 2,3-unsaturated and 2-deoxy glycosides of hindered alcohols, aryl thiols, and aryls sulfonamides from glycal derivatives under the Ferrier rearrangement conditions.
Abstract: Nitrosyl tetrafluoroborate (NOBF4) has been successfully applied as an efficient organocatalyst for the preparation of 2,3-unsaturated and 2-deoxyglycosides of hindered alcohols, aryl thiols, and aryl sulfonamides from glycal derivatives under the Ferrier rearrangement conditions. Product yields and stereo-outcomes were very good.
10 citations
TL;DR: A protected trihydroxyindolizidine 3-carboxylate was prepared by a 6-endo epoxide cleavage from the hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate to a D-ribose-derived exo-glycal.
10 citations
TL;DR: A regio- and stereo-controlled, one-pot amidoglycosylation of alcohols has been achieved using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene in the presence of a rhodium(II) catalyst.
Abstract: A regio- and stereo-controlled, one-pot amidoglycosylation of alcohols has been achieved using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene in the presence of a rhodium(II) catalyst. The reaction would proceed via stereoselective intermolecular aziridination of the glycal.
10 citations