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• W2013400595 abstract "1,2-Anhydro-3,4-di-O-benzyl-α-l-rhamnopyranose was synthesized from l-rhamnose, while the d-enantiomer was synthesized from methyl 6-deoxy-2,3-O-isopropylidene-α-d-mannopyranoside. For both of the syntheses, the key intermediates were 2-O-acetyl-3,4-di-O-benzyl-α-d- and -α-l-rhamnopyranosyl chlorides that were quantitatively prepared from the corresponding diacetates by chlorination. Ring closure of the chlorides was carried out readily with potassium tert-butoxide in oxolane, and crystalline 1,2-anhydro-3,4-di-O-benzyl-β-d- and β-l-rhamnopyranose were obtained in high yields. Conformational calculations, which were carried out using vicinal proton-proton coupling constants by the modified Karplus equation, suggested that the conformations of the pyranose rings of the title compounds were basically a half chair (4H5) with some flattening at C-4. Force-field calculations (MMP2) confirmed the experimental conformation with good agreement. The coupling reaction of the 1,2-anhydro-l-rhamnose ether with 1,2;3,4-di-O-isopropylidene-α-d-galactopyranose was effected in oxolane by catalysis by a Lewis acid, and only the α-linked disaccharide was obtained." @default.
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• W2013400595 date "1993-02-01" @default.
• W2013400595 modified "2023-09-23" @default.
• W2013400595 title "Synthesis, conformational analysis, and the glycosidic coupling reaction of substituted 2,7-dioxabicyclo[4.1.0]heptanes: 1,2-anhydro-3,4-di-O-benzyl-β-l- and β-d-rhamnopyranoses" @default.
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• W2013400595 doi "https://doi.org/10.1016/0008-6215(93)84176-7" @default.
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