期刊文献+

3-(二甲基叔丁基硅氧基)戊二酸酐的合成 被引量:1

Synthesis of 3-(tert-Butyldimethylsilyloxy)glutaric anhydride
下载PDF
导出
摘要 介绍了以柠檬酸为起始原料合成3-(二甲基叔丁基硅氧基)戊二酸酐的方法。该路线经脱羧反应、加氢还原、羟基保护、酯水解和再闭环,以总收率为30.3%得到目的产物。同时讨论了合成过程中发烟硫酸的浓度、加氢还原的催化剂、反应时间对环合收率的影响,得到合成3-(二甲基叔丁基硅氧基)戊二酸酐的的适宜条件。认为该法工艺路线简单,是适合工业生产的合成路线。 3-(tert-Butyldimethylsilyloxy)glutaric anhydride, as an important drug intermediate, is synthesized from citric acid by decarboxylation, reduction, hydroxyl protection, esterolysis, cyclization, with the total yield of 30.3%. The effects of the concentration of fuming sulfuric acid, hydrogenation catalysts, reaction time on cyclization are also investigated, and the optimum condition of this synthesis is got. The results show that this simple technique has many advantages in industry.
出处 《浙江科技学院学报》 CAS 2008年第2期107-109,共3页 Journal of Zhejiang University of Science and Technology
关键词 柠檬酸 脱羧反应 氢化 闭环 citric acid decarbaoxylic reation hydrogenation cyclization
  • 相关文献

参考文献10

  • 1张志敏,方正,李长春.匹伐他汀钙的合成方法研究进展[J].合成化学,2007,15(5):536-542. 被引量:3
  • 2刘国庆,蒋成君,陈光顺.瑞舒伐他汀合成路线图解[J].中国医药工业杂志,2005,36(9):585-587. 被引量:4
  • 3[3]KONOIKE Toshiro,ARAKI Yoshitaka.Practical Synthesis of Chiral Synthons for the Preparation of HMG-CoA Reductase Inhibitors[J].J Org Chem,1994,59(25):7849-7854.
  • 4[4]ACEMOGLU Murat,RISS Bernhard.Process for the manufacture of HMG-COA reductase inhibitors,WO:03064392[P].2003-08-07.
  • 5[5]EDGAr Kingdon Hamilton,GEORGE Lukacs.Lower alkyl ester of acetonedicarboxylic acid,US:2887508[P].1959-05-19.
  • 6[6]WALTON J Smith.production of deto esters,US:2848480[P].1958-08-19.
  • 7[7]D'SA B A,MCLEOD D,VERKADE J G.Nonionic Superbase-Catalyzed Silylation of Alcohols[J].J Org Chem,1997,62(15):5057-5061.
  • 8[8]SANTANIELLOEnzo,CHIARI Marcella,FERRA-BOSCHI,et al.Enhanced and reversed enantioselectivity of enzymic hydrolysis by simple substrate modifications:the case of 3-hydroxyglutarate diesters[J].J Org Chem,1988,53(7):1567-1569.
  • 9[9]ARNAUD Nathalie,PICARD Claude,CAZAUX Louis,et al.Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and β-hydroxyglutaric acid[J].Tetrahedron,1997,53(40):13757-13768.
  • 10[10]TOSHIRO Konoike,ETSUO Okada,YOSHITAKA Araki.Optical Resolution of 3-(Silyloxy) Glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor[J].J Org Chem,1998,63(9):3037-3040.

二级参考文献36

  • 1封宇飞,雷静,吕俊玲,孙春华.新型降酯药——罗伐他汀[J].中国临床药理学杂志,2004,20(3):234-236. 被引量:2
  • 2何笑荣,邹定,姜文清,马捷,李金娥.降血脂新药匹伐他汀[J].中国新药杂志,2005,14(4):483-487. 被引量:31
  • 3Crabb JN, Horbury J, Taylor NP. Improved production of rosuvastatin calcium salt[P]. WO: 2004108691, 2004-12-16. (CA 2005, 142: 56338)
  • 4Hirai K, Ishiba T, Koike H, et al. Pyrimidine derivatives [P].EP: 521471, 1991-01-07. (CA 1993, 118: 254949)
  • 5Quirk J, Thornton M, Kirkpatrick P. Rosuvastatin calcium [J]. Nat Rev Drug Discov, 2003, 2 (10): 769-770.
  • 6Watanabe M, Koike H, Ishiba T, et al. Synthesis and biological activity of methanesulfonamide pyrimidine- and Nmethanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates, a novel series of HMG-CoA reductase inhibitors [J]. Bioorg Med Chem, 1997, 5 (2): 437-444.
  • 7Nicole E, Yvonne R. Process for the preparation of pyrimidine derivatives[P]. WO: 2004103977, 2004-12-02. (CA 2005, 142: 23301)
  • 8Konoike T, Araki Y. Practical synthesis of chiral synthons for the preparation of HMG-CoA reductase inhibitors [J]. J Org Chem, 1994, 59(25): 7849-7854.
  • 9Carswell CI, Plosker GL, Jarvis B. Josuvastatin [J]. Drugs,2002, 62 (14): 2075-2085.
  • 10Matsushita A, Oda M, Kawachi Y, et al. Preparation of aminopyrimidine compounds [P]. WO: 2003006439, 2003-01-23. (CA 2003, 138: 122651)

共引文献5

同被引文献28

  • 1王强,潘红娟,袁哲东.雷尼酸锶的合成[J].中国医药工业杂志,2007,38(2):76-77. 被引量:6
  • 2周贤言,潘联根.一种丙酮二羧酸二甲酯的制备方法.[P].CN101475482A.2009.
  • 3Karine Audouze, Elsebet Ostergaard Nielsen. New Ligands with Affinity for the a4β2 Subtype of Nicotinic Acetylcholine Receptors. Synthesis, Receptor Binding, and 3D - QSAR Modeling. [J]. J. Med. Chem. , 2006, 49:3 159-3 171.
  • 4Masatoshi Shibuya, Masaki Tomizawa, Yusuke Sasano. An Expeditious Entry to 9 - Azabicuclo [ 3,3,1 ] nonane N - Oxyl ( ABNO ) : Another Highly Active Organocatalyst for Oxidation of Alcohols. [ J ]. J. Org. Chem. , 2009, 74:4 619 - 4 622.
  • 5John E Burks, Leandro Esoinosa, Elizabeth S Labell. Development of Manufacturing Process for Zatosetron Maleate. [ J]. Organic Process Research & Development, 1997 ( 1 ) : 198 - 210.
  • 6Vladimir F Kuznetsov. Method for Synthesizing 2 - Carbomethoxytropinone[P]. US 7855296 B1,2010 -12 -21.
  • 7Sebastian Heiner, Heiner Detert, Axel Kuhn. Hydrophilic photolabelling of glycopeptides from the murine liver - intestine(LI) cadherin recognition domain. [ J]. Bioorganic & Medicinal Chemistry, 2006 (14) : 6 149-6 164.
  • 8Dustin J Maly, Francesco Leonetti, Bradley J Backes. Expedient Solid - Phase Synthesis of Fluorogenic Protease Substrates Using the 7 - amino - 4 - carbamoylmethylcoumarin ( ACC ) Fluorophore [ J ]. J. Org. Chem. , 2002, 67:910-915.
  • 9Newman A H, Allen A C, Izenuasser S. Novel 3a - (Diphenylmethoxy) tropane Analogs: Potent Dopamine Uptake Inhibitors without Cocaine - like Behavioral Profiles [ J ]. J Med Chem, 1994,37 ( 15 ) : 2 258 -2 263.
  • 10Javad Azizian, Ali A. Mohammadi, Ilyar Bidar. KAl( SO4 )2 · 12H2O(alum) a reusable catalyst for the synthesis of some 4 -substituted coumatins via Pcchmann reaction under solvent -free conditions[ J ]. Monatsh Chem. , 2008,139: 805 -808.

引证文献1

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部