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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A new Oxyma derivative for nonracemizable amide-forming reactions in water
Qinghui Wang1, Yong Wang, Michio Kurosu
1Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 881 Madison, Memphis, Tennessee 38163-0001, USA.
Abstract:
An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO(3) in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.
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