Nucleophilic Substitution Versus Radical Reaction for Carbohydrates Deoxygenation: Application at c-4 of Methyl-α-D-Glucopyranoside Derivatives
- 1 January 1995
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 14 (1) , 157-163
- https://doi.org/10.1080/07328309508006442
Abstract
Two methods for deoxygenation at C-4 of methyl 2,3-di-O-benzyl-α-d-glucopyranoside are reported. The first one involves nucleophilic displacement of a secondary methane sulfonate by lithium triethylborohydride to afford methyl 2,3-di-O-benzyl-4-deoxy-α-d-xylo-hexopyranoside (5). Compound 5 was also obtained in similar yield (=60%) by radical deoxygenation with tri-n-butyltin hydride of a thiocarbonylated derivative.Keywords
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