Stereoselective synthesis of a C-glycosylic compound (a "methyl C-glycoside") through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination |
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Authors: | Shanmugasundaram Bhagavathy Varghese Babu Balasubramanian Kalpattu K |
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Institution: | Department of Chemistry, Indian Institute of Technology, Madras, 600 036, Chennai, India. |
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Abstract: | Readily available 3,4,6-tri-O-acetyl-D-glucal was converted to 2,6-anhydro-5,7-O-benzylidene-1,3,4-trideoxy-D-arabino-hept-3-enitol, a methyl C-glycosylic compound. Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2,6-anhydro-1-deoxyheptose, (a "methyl C-beta-D-glycoside"). The stereochemistry of the 1,2-cyclopropano sugar and the "methyl C-glycoside" were confirmed by single-crystal X-ray diffraction studies. |
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Keywords: | C-Glycoside 1 2-Cyclopropanated sugar Radical ring opening Single-crystal X-ray diffraction |
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