The Journal of organic chemistry

4, 6-O-[1-Cyano-2-(2-iodophenyl) ethylidene] acetals. Improved second-generation acetals for the stereoselective formation of β-D-mannopyranosides and …

D Crich, AA Bowers

Index: Crich, David; Bowers, Albert A. Journal of Organic Chemistry, 2006 , vol. 71, # 9 p. 3452 - 3463

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Citation Number: 48

Abstract

The [1-cyano-2-(2-iodophenyl)] ethylidene group is introduced as an acetal-protecting group for carbohydrate thioglycoside donors. The group is easily introduced under mild conditions, over short reaction times, and in the presence of a wide variety of other protecting groups by the reaction of the 4, 6-diol with triethyl (2-iodophenyl) orthoacetate and camphorsulfonic acid, followed by trimethylsilyl cyanide and boron trifluoride etherate. The new protecting ...