Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters |
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Authors: | Murakami Teiichi Sato Yukari Shibakami Motonari |
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Institution: | aInstitute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan |
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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 ZnI2 to give the corresponding 1,2-trans-β-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis- -glucosides were selectively formed. |
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Keywords: | Glycosylation Disarmed glycosyl halides Lewis acids NBS Anomer |
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