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

Alexander I Zinin; Nelly N Malysheva; Anna M Shpirt; Vladimir I Torgov; Leonid O Kononov

doi:10.1016/j.carres.2006.10.009

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

Carbohydr Res. 2007 Feb 26;342(3-4):627-30. doi: 10.1016/j.carres.2006.10.009. Epub 2006 Oct 13.

Authors

Alexander I Zinin¹, Nelly N Malysheva, Anna M Shpirt, Vladimir I Torgov, Leonid O Kononov

Affiliation

¹ N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991 Moscow, Russian Federation.

PMID: 17118348
DOI: 10.1016/j.carres.2006.10.009

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry*
Benzylidene Compounds / chemistry*
Borohydrides / chemistry
Mesylates / chemistry*
Oxidation-Reduction

Substances

Acetals
Benzylidene Compounds
Borohydrides
Mesylates
methanesulfonic acid
sodium cyanoborohydride