137743-46-5Relevant academic research and scientific papers
Manipulating the Stoichiometry and Strength of Phosphodiester Binding to a Bisguanidine Cleft in DMSO/Water Solutions
Ariga, Katsuhiko,Anslyn, Eric V.
, p. 417 - 419 (1992)
A cleft with two aminoimidazoline groups preorganized to form a V-shaped cavity was found to bind dibenzyl phosphate in mixtures of DMSO and water.
T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates
Janczewski, ?ukasz,Gajda, Anna,Frankowski, Sebastian,Goszczyński, Tomasz M.,Gajda, Tadeusz
, p. 1141 - 1151 (2017/12/06)
A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.
Versatile synthesis of 2′-amino-2′-deoxyuridine derivatives with a 2′-amino group carrying linkers possessing a reactive terminal functionality
Gondela, Andrzej,Tomczyk, Mateusz D.,Przypis, ?ukasz,Walczak, Krzysztof Z.
, p. 5626 - 5632 (2016/08/17)
2,2′-Anhydrouridine has been successfully converted into the appropriate 2′-amino-2′-deoxyuridine derivatives in a reaction with isothiocyanates obtained from amino acids or α,ω-diaminoalkanes. The initially formed oxazolidine-2-thione ring is cleaved under basic conditions into the corresponding 2′-amino(substituted)-2′-deoxyuridine derivatives. The implemented additional terminal functionality in the substituent attached to the 2′-amino group allows further modifications with e.g., fluorophore moiety.
N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
supporting information; experimental part, p. 5260 - 5266 (2009/12/06)
(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate
Munch, Henrik,Hansen, Jon S.,Pittelkow, Michael,Christensen, J?rn B.,Boas, Ulrik
, p. 3117 - 3119 (2008/09/20)
Alkyl and aryl amines are converted smoothly to the corresponding isothiocyanates via the dithiocarbamates in good to excellent yields using di-tert-butyl dicarbonate (Boc2O) and 1-3 mol % of DMAP or DABCO as catalyst. As most of the byproducts are volatile, the work-up involves simple evaporation of the reaction mixture.
Bis(alkylguanidinium) receptors for phosphodiesters: Effect of counterions, solvent mixtures, and cavity flexibility on complexation
Kneeland, Diane M.,Ariga, Katsuhiko,Lynch, Vincent M.,Huang, Chia-Yu,Anslyn, Eric V.
, p. 10042 - 10055 (2007/10/02)
Four bis(guanidinium) receptors have been synthesized in which the guanidinium groups are spatially preorganized by an octahydroacridine (meso-3 and d,l-3) or hexahydrodicyclopenta[b,e]pyridine (meso-4 and d,l-4) spacer to complement a phosphodiester. The
