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  • Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters.

Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters.

Carbohydrate research (2008-04-15)
Teiichi Murakami, Yukari Sato, Motonari Shibakami
ABSTRACT

Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI(2) to give the corresponding 1,2-trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Zinc bromide, puriss., anhydrous, ≥98%
Pricing and availability is not currently available.
Sigma-Aldrich
Zinc bromide, AnhydroBeads, −10 mesh, 99.999% trace metals basis
Pricing and availability is not currently available.
Sigma-Aldrich
Zinc bromide, 99.999% trace metals basis
Pricing and availability is not currently available.