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Über die Iodierung von Monosaccharid‐Derivaten mit Iodtrimethylsilan
Author(s) -
Klemer Almuth,
Bieber Michael
Publication year - 1984
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198419840523
Subject(s) - chemistry , anomer , monosaccharide , trimethylsilyl , iodine , halogenation , ether , iodide , yield (engineering) , medicinal chemistry , organic chemistry , materials science , metallurgy
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).