Über die Iodierung von Monosaccharid-Derivaten mit Iodtrimethylsilan

✍ Scribed by Klemer, Almuth ;Bieber, Michael

• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: English
• Weight: 256 KB
• Volume: 1984
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198419840523

✦ Synopsis

Iodation of Monosaccharide Derivatives with Iodotrimethylsilane

With iodotrimethylsilane generated in situ, 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‐O‐acetyl‐D‐glucopyranoses 1a–d decreases in the following series: OAc > OBz ≈ OH » OCH~3~. – Hydroxy groups or their ethers 3b, c react distinctively to give the trimethylsilyl ethers, whereas the primary react to yield the 6‐deoxy‐6‐iodo derivatives 5. The 1‐O‐acetyl‐6‐hydroxy derivative 6a and its 6‐O‐trityl ether form 2,3,4‐tri‐O‐acetyl‐6‐deoxy‐6‐iodo‐α‐D‐glucopyranosyl iodide (7).