Generic placeholder image

Letters in Organic Chemistry

Author(s): Takashi Yamanoi, Yoshiki Oda, Ippo Yamazaki, Masae Shinbara, Kenji Morimoto and Sho Matsuda

DOI: 10.2174/1570178053765410

DownloadDownload PDF Flyer Cite As
Sc(OTf)3 Efficiently Catalyzed the Glycosidation of 1-C-Alkyl-2,3,4,6-tetra- O-benzyl-α-D-glucopyranosyl Acetates with Alcohols

Page: [242 - 246] Pages: 5

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

Several 1-C-alkyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosides were stereoselectively synthesized in good yields by the reaction of the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-?-D-glucopyranosyl acetates with alcohols in the presence of 5 mol% Sc(OTf)3. The nature of the alkyl groups at the anomeric centers of the glycosyl donors had almost no influence on the reactivity and stereoselectivity of this glycosidation.

Keywords: alkyl-glycoside, glycosidation, glycosyl acetate, ketoside, lewis acid