title: Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters.
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.
authors.affiliation: Institute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan. t-murakami@aist.go.jp
authors.forename: Teiichi
authors.initials: T
authors.lastname: Murakami
authors.forename: Yukari
authors.initials: Y
authors.lastname: Sato
authors.forename: Motonari
authors.initials: M
authors.lastname: Shibakami
mesh_terms: D001965:Bromides / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D006219:Halogens / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D001965:Bromides; D005960:Glucosides; D006219:Halogens; D007454:Iodides; D017967:Zinc Compounds; D001974:Bromosuccinimide; C093802:zinc bromide