ABH
Chemical Name: 2(S)-Amino-6-(borono)hexanoic acid
项目整合开发状态: Preclinical
项目研究机构: Boston University (Originator), Temple University (Originator), University of Pennsylvania (Originator)
合成路线:The protected glutamic acid (I) is converted to the mixed anhydride (II) using ethyl chloroformate,and subsequently reduced to alcohol (III) by means of NaBH4.Swern oxidation of (III) provides aldehyde (IV),which is subjected to a Wittig condensation with triphenyl methylenephosphorane to afford olefin (V).Hydroboration of (V),followed by reaction with (+)-pinanediol (VI) leads to the boronate (VII).Finally,complete deprotection of (VII) with BCl3 yields the desired boronic acid.
📌 参考资料/链接：
参考文献标题:Inhibition of Mn2+2-arginase by borate leads to the design of a transition state analogue inhibitor,2(S)-amino-6-boronohexanoic acid
文献作者:Ash,D.E.; Carroll,P.J.; Baggio,R.; Cavalli,R.C.; Christianson,D.W.; Kanyo,Z.F.; Elbaum,D.
参考来源:J Am Chem Soc 1997,119(34),8107
📄 详细内容
合成路线:The enantioselective alkylation of the nickel complex (I) of the Schiff base derived from glycine and (S)-2-[N'-(N-benzylprolyl)amino]benzophenone with 4-bromo-1-butene (II) affords the corresponding complex (III) of (S)-2-amino-5-hexenoic acid,which is subsequently hydrolyzed to the free aminoacid (IV) under mild acidic conditions.Esterification of (IV) by means of SOCl2 in methanol leads to amino ester (V),and further protection with di-tert-butyl dicarbonate provides the N-Boc derivative (VI).Hydroboration of the double bond of (VI) with diisopinocampheylborane,followed by in situ oxidation with acetaldehyde gives rise to the diethyl boronate (VII).This is then converted to the isolable pinanediol boronate (IX) upon treatment with (+)-pinanediol (VIII).Finally,total deprotection of (IX) by refluxing with 12 M HCl furnishes the title compound.
参考文献标题:Synthesis and evaluation of omega-borono-alpha-amino acids as active-site probes of arginase and nitric oxide synthases
文献作者:Collet,S.; et al.
参考来源:J Chem Soc - Perkins Trans I 2000,(2),177