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Polymethylhydrosiloxane (PMHS): A Convenient Option for Synthetic Applications of the Iodine/Silane Combined Reagent – Straightforward Entries to 2‐Hydroxyglycals and Useful Building‐Blocks of Glucuronic Acid and Glucosamine
Author(s) -
Giordano Maddalena,
Iadonisi Alfonso
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201084
Subject(s) - chemistry , reagent , silane , triethylsilane , combinatorial chemistry , glycosyl , iodine , glucuronic acid , organic chemistry , catalysis , polysaccharide
Polymethylhydrosiloxane (PMHS) proved to be a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. In addition, the scope of this combined reagent was expanded to the especially fast generation of 2‐acetoxyglycals, and the rapid synthesis of useful building‐blocks of D ‐glucuronic acids and D ‐glucosamine. All the synthetic targets were obtained in especially short times either via one‐pot procedures or through experimental sequences devoid of laborious chromatographical purifications of intermediates.