Journal ArticleDOI
A New Catalyst for the Reductive Elimination of Acylated Glycosyl Bromides to Form Glycals
TLDR
In this article, a useful catalyst for the reductive elimination of acylated glycosyl bromides to form glycals, both in the pyranose and furanose series, using zinc/ammonium chloride/methanol or zinc/acetic acid/acetonitrile.Abstract:
Ethylene-N,N-bis(salicylideneiminato)oxovanadium(IV) {VO(salen)} has been developed as a useful catalyst for the reductive elimination of acylated glycosyl bromides to form glycals, both in the pyranose and furanose series, using zinc/ammonium chloride/methanol or zinc/acetic acid/acetonitrile.read more
Citations
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Journal ArticleDOI
Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides.
TL;DR: Three compounds reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement were found to possess potent activity compared to hydrocortisone sodium succinate (HSS).
Journal ArticleDOI
Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors.
TL;DR: A convergent synthesis of the complex, doubly-branched pentasaccharide domain of the natural-product immunoadjuvant jujuboside A is described, withherent complete diastereoselectivity for the undesired α-anomer overcome by rational optimization with a nitrile solvent system to provide flexible, effective access to the β-linked pentasACcharide.
Journal ArticleDOI
The Synthesis of a New Class of Potential Inhibitors for Glycoside Hydrolases
Robert V. Stick,Keith A. Stubbs +1 more
TL;DR: Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described and none of these three novel compounds proved to be a significant inhibitor of a retaining α‐glucosidase from barley.
Book ChapterDOI
2.13 – Alkenyl and Aryl Chalcogenides: Oxygen-based Functional Groups
TL;DR: In this article, current methods for the preparation of alkenyl and aryl compounds bound at an sp2-carbon to oxygen are described, from the period 1993 to 2003.
Journal ArticleDOI
Synthesis and x-ray crystallographic analysis of 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hexopyranosyl cyanide.
Madeline E. Rotella,Matthew Giovine,William G. Dougherty,Walter J. Boyko,Scott Kassel,Robert M. Giuliano +5 more
TL;DR: The glycopyranosyl cyanide 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hexopyranosy cyanide has been synthesized from tri-O -acetyl -D-galactal by reaction with trimethylsilyl cyanide in the presence of boron trifluoride diethyl etherate followed by catalytic hydrogenation.
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