A novel synthesis of β-d-mannopyranosyl azide by phase transfer catalysis |
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| Authors: | Polina I Abronina |
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| Institution: | N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prospect, 47, 119991 Moscow, Russian Federation |
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| Abstract: | A simple stereoselective synthesis of per-O-benzoyl-β-d-mannopyranosyl azide from per-O-benzoyl-α-d-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated α- and β-d-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected β-d-mannopyranosyl azide was prepared by debenzoylation with sodium methoxide in methanol. |
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| Keywords: | Glycosyl azides 1 2-cis-Mannopyranosyl azide Phase transfer catalysis Stereoselectivity NMR spectroscopy |
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