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

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

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 3 , 2005

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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

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Article Details

VOLUME: 2
ISSUE: 3
Year: 2005
Page: [242 - 246]
Pages: 5
DOI: 10.2174/1570178053765410
Price: $65

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