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  • Regioselective debenzylation of C-glycosyl compounds by boron trichloride.

Regioselective debenzylation of C-glycosyl compounds by boron trichloride.

Carbohydrate research (2005-02-01)
Juan Xie, Mickaël Ménand, Jean-Marc Valéry
ABSTRACT

Boron trichloride has been found to promote selective deprotection of 1,2- or 1,3-cis oriented secondary benzyl ethers of per-benzylated C-glycosyl derivatives. The reactivity towards BCl(3) follows the order: C-4>or=C-2>C-6>C-3 for C-glucopyranosyl derivatives and C-3>or=C-4>C-6>C-2 for C-galactopyranosyl derivatives. Preparatively useful selective debenzylation at secondary positions was possible after careful control of reaction conditions.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Boron trichloride solution, 1.0 M in toluene
Sigma-Aldrich
Boron trichloride solution, 1.0 M in heptane
Sigma-Aldrich
Boron trichloride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Boron trichloride solution, 1.0 M in p-xylene