Citation: Wang Yongsheng, Zhao Ling, Wang Tao, Liu Rong. Progress in the Synthesis of (R)-3-Amino-1-butanol[J]. Chemistry, ;2018, 81(11): 986-991. shu

Progress in the Synthesis of (R)-3-Amino-1-butanol

Wang Yongsheng ^1,2, ,
Zhao Ling ³ ,
Wang Tao ^1,2 ,
Liu Rong ^1,2,,

1.
Gansu Chemical Industry Research Institute Co., Ltd., Lanzhou 730020
2.
Gansu Key Laboratory of Fine Chemicals, Lanzhou 730020
3.
Department of Pathology, Lanzhou University Second Hospital, Lanzhou 730020

Corresponding author: Liu Rong, elitelori@hotmail.com
Received Date: 14 June 2018
Accepted Date: 20 August 2018

As a key intermediate for the synthesis of HIV intergrase inhibitors dolutegravir, the quality and price of (R)-3-amino-1-butanol have a significant impact on the quality and production cost of dolutegravir. In this paper, the synthesis of (R)-3-amino-1-butanol was reviewed from five aspects:chemical resolution, chiral synthesis, chemical induction, preparative chromatograph and enzymatic hydrolysis.
- (R)-3-amino-1-butanol,
- Dolutegravir,
- 4-Hydroxy-2-butanone,
- Transaminas
1. [1]
2. [2]
3. [3]
  B A Johns, T Kawasuji, T Taishi et al. WO:2006/116764A1.
4. [4]
  D N Rhyne, E S Byrd, O M Klibanov. Nurse Pract., 2014, 39(6):11~15.
5. [5]
  D J Cada, T L Levien, D E Baker. Hosp. Pharm., 2014, 49(2):184~195.
6. [6]
  S Hare, S J Smith, M Metifiot et al. Mol. Pharmacol., 2011, 80(4):565~572.
7. [7]
8. [8]
  D A Cooper, R T Steigbigel, J M Gatell et al. New Engl. J. Med., 2008, 359(4):355~365.
9. [9]
10. [10]
  M Breuer, K Ditrich, H Winsel. US:2011/0275855A1.
11. [11]
  R Y Srinivasa, I Aminual, D Nageshwar. Heterocyclic Lett., 2015, 5(2):241~244.
12. [12]
  S Tatsuya, K Naoki, S Fumio et al. Tetrahed. Lett., 1988, 29(2):231~234.
13. [13]
  M Achmatowicz, A Szumna, T Zieliński et al. Tetrahedron, 2005, 61(38):9031~9041.
14. [14]
  R Kinas, K Pankiewicz, W J Stec et al. J. Org. Chem., 1977, 42(9):1650~1652.
15. [15]
  C Andrés, A González, R Pedrosa. Tetrahed. Lett., 1992, 33(20):2895~2898.
16. [16]
  W Volkmar, B Horst, R Hartmut et al. US:2003/0073723A1.
17. [17]
  R Albers, L Ayala, S Clareen et al. WO:2006/076595A1.
18. [18]
  W Kuriyama, Y Ino, O Ogata. Adv. Synth. Catal. 2010, 352(1):92~96.
19. [19]
  A B Haitham. WO:2010/063294A1.
20. [20]
21. [21]
22. [22]
  V N Bodil, B Fauber, S Gaines et al. WO:2014/009447A1.
23. [23]
  B Fauber, O Rene. WO:2014/202741A1.
24. [24]
  O Rene, B Fauber, D Vesey et al. WO:2017/005668A1.
25. [25]
  B Pascale, C Stéphane, J L Canetb. Tetrahedron:Asymmetry, 1999, 10(11):2213~2224.
26. [26]
27. [27]
  A G Khatik, M Husain. WO:2018/020380A1.
1. [1]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
2. [2]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
3. [3]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
4. [4]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
5. [5]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
6. [6]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
7. [7]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
8. [8]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
9. [9]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . Construction of 4-Amino-1H-imidazole-5-carbonitrile Modified Carbon Nitride-Based Donor-Acceptor Photocatalyst for Efficient Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-0. doi: 10.3866/PKU.WHXB202406026
10. [10]
  Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoS_x assembled from [Mo₃S₁₃]^2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
11. [11]
  Shi-Yu Lu , Wenzhao Dou , Jun Zhang , Ling Wang , Chunjie Wu , Huan Yi , Rong Wang , Meng Jin . Amorphous-Crystalline Interfaces Coupling of CrS/CoS₂ Few-Layer Heterojunction with Optimized Crystallinity Boosted for Water-Splitting and Methanol-Assisted Energy-Saving Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(8): 2308024-0. doi: 10.3866/PKU.WHXB202308024
12. [12]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
13. [13]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
14. [14]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
15. [15]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
16. [16]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
17. [17]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
18. [18]
  Fei ZHOU , Xiaolin JIA . Co₃O₄/TiO₂ composite photocatalyst: Preparation and synergistic degradation performance of toluene. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2232-2240. doi: 10.11862/CJIC.20240236
19. [19]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
20. [20]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-0. doi: 10.3866/PKU.WHXB202408005

Get Citation

PDF

XML

Metrics

PDF Downloads(36)
Abstract views(1637)
HTML views(613)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142