Rapid preparation of variously protected glycals using titanium (III)

…, CL Cavallaro, J Schwartz

Index: Spencer, Roxanne P.; Cavallaro, Cullen L.; Schwartz, Jeffrey Journal of Organic Chemistry, 1999 , vol. 64, # 11 p. 3987 - 3995

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Citation Number: 55

Abstract

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti [III] Cl) 2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid-and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction ...

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