MilliporeSigma
  • DIBALH mediated reduction of the acetal moiety on perhydrofuro[2,3-b]pyran derivatives.

DIBALH mediated reduction of the acetal moiety on perhydrofuro[2,3-b]pyran derivatives.

Carbohydrate research (2001-09-13)
J Marco-Contelles, J Ruiz-Caro
ABSTRACT

The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built on these substrates remain practically or partially unaltered in these conditions depending on the steric volume of the O-protecting group located at C-4 (TBDMS vs. Me). This protocol can be considered as a new entry for the synthesis of chiral and highly functionalized cyclopentanes.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in toluene
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in hexanes
Sigma-Aldrich
Diisobutylaluminum hydride solution, 25 wt. % in toluene
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in heptane
Sigma-Aldrich
Diisobutylaluminum hydride, reagent grade
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in THF
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in cyclohexane