- Synthesis of vinylic C-glycosides from telluroglycosides. Addition of photochemically and thermally generated glycosyl radicals to alkynes
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Glycosyl radicals generated from telluroglycosides react with a variety of alkynes to give the corresponding vinylic C-glycosides in good to excellent yields. The reaction takes place in an atom transfer manner to form vinyl telluride, and the resulting C-Te bond is transmetalated to the C-Zn bond with Et2Zn or reduced to the C-H bond with tributyltin hydride.
- Yamago, Shigeru,Miyazoe, Hiroshi,Yoshida, Jun-ichi
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- Knoevenagel condensation between C-glycoside and active methylene compounds without catalysts
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A Knoevenagel condensation reaction between a C-glycoside based aromatic aldehyde and cyclic active methylene compounds such as barbituric acid, thiobarbituric acid, 1,3-dimethylbarbituric acid, 5,5-dimethyl-1,3-cyclohexanedione, 2,2-dimethyl-1,3-dioxane-
- Gu, Xiaomin,Fang, Zhijie
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- Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes
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A mild, stereoselective method for the Ni-catalyzed synthesis of α-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.
- Gong, Hegui,Andrews, R. Stephen,Zuccarello, Joseph L.,Lee, Stephen J.,Gagne, Michel R.
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supporting information; experimental part
p. 879 - 882
(2009/07/25)
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- Effective friedel-crafts acylations of O- and C-arylglycosides with triflic acid
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Triflic acid is well known not only as a Friedel-Crafts promoter, but also as a deglycosidation reagent. In this study, we promote effective Friedel-Crafts acylations for O- or C-arylglucosides without deglycosidation and check their inhibitory activities for β-glucosidase.
- Hashimoto, Makoto,Takahashi, Miho
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body text
p. 227 - 231
(2009/09/06)
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- O-Glycosyl Imidates, 19. - Reactions of Glycosyl Trichloroacetimidates with Silylated C-Nucleophiles
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Reaction of O-benzyl-protected α-glycopyranosyl trichloroacetimidates 1 and the xylo analogues 7 with silyl enol ethers or allyltrimethylsilane as C-nucleophiles yields with zink chloride as catalyst mainly or exclusively α-C-glycosides (5a-α to 5h-α, 8b,
- Hoffmann, Michael G.,Schmidt, Richard R.
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p. 2403 - 2419
(2007/10/02)
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