Use of methanesulfonic acid in the reductive ring-opening of O-benzylidene acetals

…, NN Malysheva, AM Shpirt, VI Torgov, LO Kononov

Index: Zinin, Alexander I.; Malysheva, Nelly N.; Shpirt, Anna M.; Torgov, Vladimir I.; Kononov, Leonid O. Carbohydrate Research, 2007 , vol. 342, # 3-4 p. 627 - 630

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Citation Number: 17

Abstract

Methanesulfonic acid was shown to be an efficient and convenient substitute for ethereal HCl in reductive 4, 6-O-benzylidene acetal ring-opening reaction with sodium cyanoborohydride in THF. Normal regioselectivity was observed, the 6-O-benzyl ethers with free 4-OH group being the major products of the reaction.