Description:
<jats:p><jats:bold>Iodation of Monosaccharide Derivatives with Iodotrimethylsilane</jats:bold></jats:p><jats:p>With iodotrimethylsilane generated <jats:italic>in situ</jats:italic>, iodine can be introduced into carbohydrate derivatives with high selectivity. The rate of iodination at the anomeric center of the C‐1‐substituted 2,3,4,6‐tetra‐<jats:italic>O</jats:italic>‐acetyl‐<jats:sc>D</jats:sc>‐glucopyranoses <jats:bold>1a</jats:bold>–<jats:bold>d</jats:bold> decreases in the following series: OAc > OBz ≈ OH » OCH<jats:sub>3</jats:sub>. – Hydroxy groups or their ethers <jats:bold>3b, c</jats:bold> react distinctively to give the trimethylsilyl ethers, whereas the primary react to yield the 6‐deoxy‐6‐iodo derivatives <jats:bold>5</jats:bold>. The 1‐<jats:italic>O</jats:italic>‐acetyl‐6‐hydroxy derivative <jats:bold>6a</jats:bold> and its 6‐<jats:italic>O</jats:italic>‐trityl ether form 2,3,4‐tri‐<jats:italic>O</jats:italic>‐acetyl‐6‐deoxy‐6‐iodo‐α‐<jats:sc>D</jats:sc>‐glucopyranosyl iodide (7).</jats:p>