1365536-84-0Relevant academic research and scientific papers
New C-glycosylated α-amino acid synthesis by addition reaction of an amino acid organozinc reagent on carbohydrate-derived aldehydes
Boutard, Nicolas,Labeguere, Frederic,Vidal, Yves,Lavergne, Jean-Pierre,Martinez, Jean
, p. 1461 - 1471 (2012/05/05)
Two unreported C-glycosylated amino acid structures could be prepared by addition of an amino acid organozinc on carbohydrates bearing an aldehyde function. For this purpose, a new iodinated amino acid bearing a four-carbon side chain was conveniently prepared in two steps. Conversion into the corresponding organozinc reagent was optimal in acetonitrile using zinc/copper activated with 1,2-dibromoethane and trimethylsilyl chloride. A protocol was developed for the addition of this organozinc compound to simple aldehydes in acetonitrile using BF3 · OEt2 as a Lewis acid. When applied to riboside and glucoside aldehyde derivatives, this protocol led to new C-glycosylated amino acids in acceptable yields. Copyright Taylor & Francis Group, LLC.
