Journal ArticleDOI
A one-step method for the preparation of 2-pyridyl 2-deoxy-1-thiohexopyranosides from glycal esters
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This article is published in Carbohydrate Research.The article was published on 1987-10-15. It has received 9 citations till now. The article focuses on the topics: Glycal.read more
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Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry
Tetrahedron report number 754 Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry
L. F. Awad,A. I. Atta +1 more
Journal ArticleDOI
Synthesis of double-chain bis-sulfone neoglycolipids of the 2″-, 3″-, 4″-, and 6″-deoxyglobotrioses
Zhang Zhiyuan,Göran Magnusson +1 more
TL;DR: Glycosylation of 3-(hexadecylsulfonyl-2]-propanol with the trichloroacetimidates, followed by removal of protecting groups, gave the title neoglycolipids.
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Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator
TL;DR: In this paper, a practical and highly stereoselective glycosidation methodology is described, where anomeric mixture of 2-deoxy 2-pyridyl-1-thiopyranoside donors have been coupled with several sugar alcohols on activation by methyl iodide to obtain axially linked 2deoxysaccharides.
Journal ArticleDOI
A highly selective route to β-C-glycosides via nonselective samarium iodide induced coupling reactions
TL;DR: Stereoselective preparation of beta-C-glycosides has been developed from acetylated glycopyranosyl 2-pyridyl sulfones, involving a samarium-Barbier coupling procedureoxidation-isomerization sequence.
References
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Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a
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A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using dast. Preparation of glycosyl fluorides.
Gary H. Posner,Stephen R. Haines +1 more
TL;DR: The anomeric hydroxyl group of various furanose and pyranose hemiacetals can be replaced by a fluorine atom stereoselectively, conveniently, mildly, and on gram-scale using DAST in THF at room temperature.
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Asymmetric total synthesis of erythromycin. 3. Total synthesis of erythromycin
TL;DR: In this paper, the authors reported the synthesis of erythromycin (2) from la in optically active form, which involves the glycosidation of a suitable derivative of la with L-cladinose and D-desosamine and the generation of the C-9 ketone functionality.
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A new method for the synthesis of glycosyl fluorides
TL;DR: In this paper, Diethylamino-sulfur trifluoride (DAST) has been found to react with the free anomeric hydroxyl of suitably protected aldoses and ketoses to afford glycosyl fluorides.