Synthesis, crystal structure, and reactivity of a D-xylose based oxepine |
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Authors: | Peczuh Mark W Snyder Nicole L Sean Fyvie W |
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Institution: | Department of Chemistry, The University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA. peczuh@uconn.edu |
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Abstract: | The synthesis and X-ray crystal structure of a D-xylose-based oxepine are reported. The oxepine was prepared from 2,3,4-tri-O-benzyl-D-xylose by the three-step sequence (Wittig olefination, vinyl ether formation, and ring closing metathesis) we recently reported. Epoxidation of this cyclic enol ether using dimethyldioxirane (DMDO) gave 1,2-anhydro-beta-D-idoseptanose, which was trapped by a number of nucleophiles to give alpha-idoseptanosides. The stereochemistry of epoxidation was assigned based on product analysis. Spectroscopic data of methyl 2,3,4,5-tetra-O-acetyl-alpha-D-idoseptanoside, derived from the methanolysis product 11, was compared to data of its enantiomer, the known methyl 2,3,4,5-tetra-O-acetyl-alpha-L-idoseptanoside. |
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Keywords: | Septanose carbohydrates Oxepine d-Idoseptanoside" target="_blank">d-Idoseptanoside Glycosylation |
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