1-脱氧野尻霉素的N-取代苯丙烷衍生物的合成  

Synthesis of N-Substituted Phenylpropane Derivatives of 1-Deoxynojirimycin

作　　者：王峰峰 方志杰[1] WANG Fengfeng;FANG Zhijie(College of Chemistry and Chemical Engineering,Nanjing University of Science and Technology,Nanjing 210014,China)

机构地区：[1]南京理工大学化学与化工学院,江苏南京210014

出　　处：《化学与生物工程》2022年第4期52-55,共4页Chemistry & Bioengineering

摘　　要：以(2R,3R,4R,5S)-3,4,5-三(苄氧基)-2-((苄氧基)甲基)哌啶盐酸盐为起始原料,与取代苯乙酮及多聚甲醛在无水乙醇中经曼尼希反应缩合得到中间体1-(4-取代苯基)-3-((2R,3R,4R,5S)-3,4,5-三(苄氧基)-2-((苄氧基)甲基)哌啶-1-基)丙烷-1-酮,该中间体经Pd(OH)_(2)/C加氢、脱苄、脱氧得到1-脱氧野尻霉素(DNJ)的N-取代苯丙烷衍生物,总收率36.8%~46.8%,并通过^(1)HNMR、^(13)CNMR、LC-MS对产物结构进行了确证。Firstly,we synthesized the intermediate of 1-(4-substituted phenyl)-3-((2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-((benzyloxy)methyl)piperidine-1-yl)propane-1-one from(2R,3R,4R,5S)-3,4,5-tri(benzyloxy)-2-((benzyloxy)methyl)piperidine hydrochloride,substituted acetophenone,and paraformaldehyde by Mannich reaction in ethanol.Then,we synthesized the N-substituted phenylpropane derivatives of 1-deoxynojirimycin(DNJ)by Pd(OH)_(2)/C hydrogenation,debenzylation,and deoxygenation from the intermediate.The total yield can reach 36.8%-46.8%.Moreover,the structures of the products are confirmed by ^(1)HNMR,^(13)CNMR,and LC-MS.

关 键 词：(2R 3R 4R 5S)-3 4 5-三(苄氧基)-2-((苄氧基)甲基)哌啶盐酸盐 曼尼希反应 催化氢化 1-脱氧野尻霉素(DNJ) N-取代苯丙烷衍生物 

分 类 号：O626.23[理学—有机化学]