2005
DOI: 10.1055/s-2005-868500
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Synthesis of Stable Carbohydrate Mimetics as Potential Glycotherapeutics

Abstract: S y n t h e s i s o f S t a b l e C a r b o h y d r a t e M i m e t i c sAbstract: The synthesis of a variety of stable carbohydrate mimetics using a RCM approach is discussed. An esterification-RCM approach has been utilized for the preparation of a variety of alkyl, aryl b-C-glycosides as well as a number of b-C-saccharides.

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Cited by 44 publications
(17 citation statements)
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“…The resulting residue was purified by flash chromatography (60 % EtOAc/hexane) to give desired hemiacetal 5 (3.21 g, 68 %). 1 …”
Section: Methodsmentioning
confidence: 97%
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“…The resulting residue was purified by flash chromatography (60 % EtOAc/hexane) to give desired hemiacetal 5 (3.21 g, 68 %). 1 …”
Section: Methodsmentioning
confidence: 97%
“…The mixture was stirred at that temperature for 30 min, after which time it was warmed to room temperature and stirred for 1 h. The reaction crude was then concentrated, the residue was taken up in EtOAc/hexane (1:1), and the suspension was filtered through silica gel to give after evaporation of the solvents pyranosyl chloride 5 (583 mg, 92 %). 1 General Procedure for C-1 Glycal Formation: A solution of the glycosyl chloride (1 mmol) in dry THF was cooled to the appropriate temperature and then treated with the corresponding organolithium reagent (3 equiv.). After stirring for 0.5-2 h, and once TLC analyses showed total disappearance of the starting material, the reaction mixture was quenched with a saturated aqueous solution of NH 4 Cl.…”
Section: 346-tetra-o-methyl-α-d-mannopyranosyl Chloride (5)mentioning
confidence: 99%
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“…[1,2] In comparison with glycals (e.g., 2), [3] they present an additional carbon substituent at the anomeric position (C-1) while maintaining their enol ether functionality. The former facilitates an easy retrosynthetic correlation with biologically relevant C-glycosides (e.g., 3), [4,5] whereas the enol ether moiety permits the incorporation of additional functionality in the carbohydrate entity ( Figure 1).…”
Section: Introductionmentioning
confidence: 99%