咪唑基引起缩合试剂3-(二乙氧基磷酰基)-氧-1,2,3-苯并三嗪-4(3H)-酮(DEPBT)的副反应  

Side Reaction of Condensation Reagent 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one(DEPBT) Caused by Imidazolyl Group

作　　者：沈鸿雁[1] 刘镇宁[1] 晏皖琳[1] 叶蕴华[1] 田桂玲[1] 

机构地区：[1]北京大学化学与分子工程学院教育部生物有机重点实验室,北京100871

出　　处：《高等学校化学学报》2006年第7期1289-1291,共3页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20372008)资助

摘　　要：3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one(DEPBT) condensation developed by our group is an effective organophosphorus condensation reagent for the synthesis of protected peptides containing Tyr,Ser and Thr with unprotected hydroxyl group on their side chain.Thus,DEPBT is useful for the synthesis of peptide alcohols,which have attracted much attention not only as the ligands but also as the enzyme inhibitors.A side reaction of DEPBT was found in the synthesis of Boc-β-Ala-HisOMe with unprotected imidazolyl group.In this paper,the discovery of this side reaction and the confirmation of the structure of this side product were reported.In addition,the influence of different reaction conditions on the side reaction were studied.Imidazolyl group was a key factor to cause the side reaction,excess DEPBT and high reaction temperature promoted the side reaction.3-（ Diethoxyphosphoryloxy）-1 ,2,3-benzotriazin-4（3H）-one（DEPBT） condensation developed by our group is an effective organophosphorus condensation reagent for the synthesis of protected peptides containing Tyr, Ser and Thr with unprotected hydroxyl group on their side chain. Thus, DEPBT is useful for the synthesis of peptide alcohols, which have attracted much attention not only as the ligands but also as the enzyme inhibitors. A side reaction of DEPBT was found in the synthesis of Boe-β-Ala-HisOMe with unprotected imidazolyl group. In this paper, the discovery of this side reaction and the confirmation of the structure of this side product were reported. In addition, the influence of different reaction conditions on the side reaction were studied. Imidazolyl group was a key factor to cause the side reaction, excess DEPBT and high reaction temperature promoted the side reaction.

关 键 词：3-(二乙氧基磷酰基)-氧-1 2 3-苯并三嗪-4(3H)-酮(DEPBT) 组氨酸 咪唑基 副反应 

分 类 号：O621[理学—有机化学]