Skip to Content
Merck
CN
  • Use of methanesulfonic acid in the reductive ring-opening of O-benzylidene acetals.

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

Carbohydrate research (2006-11-23)
Alexander I Zinin, Nelly N Malysheva, Anna M Shpirt, Vladimir I Torgov, Leonid O Kononov
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium cyanoborohydride solution, 1.0 M in THF
Sigma-Aldrich
Sodium cyanoborohydride solution, 5.0 M in 1 M NaOH
Sigma-Aldrich
Sodium cyanoborohydride, reagent grade, 95%