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

Title: Sc(OTf)3 Efficiently Catalyzed the Glycosidation of 1-C-Alkyl-2,3,4,6-tetra- O-benzyl-α-D-glucopyranosyl Acetates with Alcohols

Volume: 2 Issue: 3

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

Affiliation:

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

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.

Cite this article as:

Yamanoi Takashi, Oda Yoshiki, Yamazaki Ippo, Shinbara Masae, Morimoto Kenji and Matsuda Sho, Sc(OTf)3 Efficiently Catalyzed the Glycosidation of 1-C-Alkyl-2,3,4,6-tetra- O-benzyl-α-D-glucopyranosyl Acetates with Alcohols, Letters in Organic Chemistry 2005; 2 (3) . https://dx.doi.org/10.2174/1570178053765410