新产品编号:1307241
Chemical Name: (1R)-1-Amino-4-(amidinio)butylboronic acid dihydrochloride; L-Boroarginine dihydrochloride
项目整合开发状态: Biological Testing
项目研究机构: CNRS (Originator)
合成路线:The hydroboration of allyl bromide (I) with diisopinocampheylborane gives the 3-bromopropylboronic ester (II),which by treatment with acetaldehyde and water yields the boronic acid (III).The reaction of (III) with NaN3 and ethanol affords 3-azidoboronic acid ethyl ester (IV),which is transesterified with optically active pipanediol (V) giving the cyclic ester (VI).The homologation of (VI) with LDA,ZnCl2 and dichloromethane in THF yields the alpha-chlorobutylboronic ester (VII),which is aminated with hexamethyldisylazane (HMDS) and BuLi to provide the silylated alpha-aminoboronic ester (VIII).The desilylation of (VIII) with methanol,and its protection with benzyl chloroformate gives the protected alpha-aminoboronic ester (IX).The hydrogenation of the azido group of (IX) with H2 over PtO2 affords the 4-aminobutylboronic ester (X),which is treated with N,N'-bis(tert-butoxycarbonyl)thiourea (XI),HgCl2 and TEA in DMF to give the guanidine derivative (XII).Finally,this compound is hydrolyzed and deprotected with refluxing 6N HCl.
📌 参考资料/链接：
参考文献标题:Synthesis of boronic acid analogs of L-arginine as alternate substrates or inhibitors of nitric oxide synthase
文献作者:Lebarbier,C.; Carreaux,F.; Carboni,B.; Boucher,J.L.
参考来源:Bioorg Med Chem Lett 1998,8(18),2573
📄 详细内容
合成路线:The hydroboration of allyl bromide (I) with diisopinocampheylborane gives the 3-bromopropylboronic ester (II),which by treatment with acetaldehyde and water yields the boronic acid (III).The reaction of (III) with NaN3 and ethanol affords 3-azidoboronic acid ethyl ester (IV),which is transesterified with optically active pipanediol (V) giving the cyclic ester (VI).The homologation of (VI) with LDA,ZnCl2 and dichloromethane in THF yields the alpha-chlorobutylboronic ester (VII),which is aminated with hexamethyldisylazane (HMDS) and BuLi to provide the silylated alpha-aminoboronic ester (VIII).The desilylation of (VIII) with methanol,and its protection with benzyl chloroformate gives the protected alpha-aminoboronic ester (IX).The hydrogenation of the azido group of (IX) with H2 over PtO2 affords the 4-aminobutylboronic ester (X),which is treated with N,N'-bis(tert-butoxycarbonyl)thiourea (XI),HgCl2 and TEA in DMF to give the guanidine derivative (XII).Finally,this compound is hydrolyzed and deprotected with refluxing 6N HCl.
参考文献标题:Synthesis of a boronic acid analogue of L-ornithine
文献作者:Lebarbier,C.; et al.
参考来源:Synthesis 1996,1371