14056-07-6Relevant articles and documents
A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 3: Iodophenyltriflate Core Fragments Featuring Side Chains of Proteinogenic Amino Acids
Breinbauer, Rolf,Dobrounig, Patrick,Doler, Carina,Holzinger, Ella B.,Schreiner, Till,Steinegger, Andreas,Trobe, Melanie,Vareka, Martin
, (2022/03/02)
Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics using a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for teraryl assembly. In previous publications we have introduced the methodology of 4-iodophenyltriflates decorated with the side chains of some of the proteinogenic amino acids. We herein report the core fragments corresponding to the previously missing amino acids Arg, Asn, Asp, Met, Trp and Tyr. Therefore, our set now encompasses all relevant amino acid analogues with the exception of His. In order to be compatible with the triflate moiety, some of the nucleophilic side chains had to be provided in a protected form to serve as stable building blocks. Additionally, cross-coupling procedures for the assembly of teraryls were investigated.
Chemoselective reduction of aldehydes using decaborane in aqueous solution
Lee, Seung Hwan,Nam, Mi Hye,Cho, Min Young,Yoo, Byung Woo,Rhee, Hak June,Yoon, Cheol Min
, p. 2469 - 2474 (2007/10/03)
Reduction of aldehydes using decaborane (B10H14) in an aqueous solution gave the corresponding alcohol chemoselectively in good to high yields. Copyright Taylor & Francis Group, LLC.
Efficient and selective reduction protocols of the 2,2-dimethyl-1,3- benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols
Bajwa, Naval,Jennings, Michael P.
, p. 3646 - 3649 (2007/10/03)
Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl-1,3-benzodioxan-4- one functional group with DIBAL-H or LAH, respectively.