6308-53-8Relevant articles and documents
A convenient and efficient synthesis of dipeptidyl benzoxaboroles and their peptidomimetics
Fu, Zhengyan,He, Jiangpeng,Tong, Aiping,Xie, Yongmei,Wei, Yuquan
supporting information, p. 2843 - 2852 (2013/10/22)
We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl) phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3- phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules. Georg Thieme Verlag Stuttgart ? New York.
Solid-phase synthesis of unnatural amino acids using unactivated alkyl halides
O'Donnell, Martin J.,Lugar, Charles W.,Pottorf, Richard S.,Zhou, Changyou,Scott, William L.,Cwi, Cynthia L.
, p. 7163 - 7166 (2007/10/03)
Conditions were developed for the efficient alkylation of the resin-bound benzophenone imine of glycine with a variety of unreactive alkyl halides. Alkylations were accomplished at room temperature in NMP using the phosphazene-type base, BEMP.