(4R)-(+)-羟基-2-环戊酮合成路线 （共 21 条）
反应条件
Yield given. Multistep reaction;
参考文献
Chen, Shaoqing; Janda, Kim D.
Journal of the American Chemical Society, 1997 , vol. 119, # 37 p. 8724 - 8725
反应条件
1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 3.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 4.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 4.2: 22 h / 25 - 30 °C / Inert atmosphere 5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 6.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 7.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme
参考文献
ACTAVIS GROUP PTC EHF; KUMAR, Arvapally, Seshu; TRIVEDI, Nikhil; PRADHAN, Nitin, Sharadchandra; SHARMA, Krishnadatt
Patent: WO2012/63126 A2, 2012 ;
反应条件
1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 2: H2 / Ni2B / methanol View Scheme
参考文献
Curran, Timothy T.; Hay, David A.; Koegel, Christopher P.; Evans, Jonathan C.
Tetrahedron, 1997 , vol. 53, # 6 p. 1983 - 2004
反应条件
1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature
2: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C
3: H2 / Ni2B / methanol
4: 37 percent / Et3N, pancreatin / various solvent(s) / 27 h / Ambient temperature
View Scheme
参考文献
Watson, Timothy J.N.; Curran, Timothy T.; Hay, David A.; Shah, Ramnik S.; Wenstrup, David L.; Webster, Mark E.
Organic Process Research and Development, 1998 , vol. 2, # 6 p. 357 - 365
反应条件
1: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 16 h / 0 - 25 °C / |Large scale
2: lithium aluminium tetrahydride; lithium iodide / toluene; tert-butyl methyl ether / 3 h / -30 °C / |Inert atmosphere; |Large scale
3: triethylamine; Pancreatin / tert-butyl methyl ether / 7 h / |Inert atmosphere; |Large scale; |Enzymatic reaction
4: hydrogen; 5 Pt/Al2O3
View Scheme
参考文献
Watson, Timothy J.N.; Curran, Timothy T.; Hay, David A.; Shah, Ramnik S.; Wenstrup, David L.; Webster, Mark E.
Organic Process Research and Development, 1998 , vol. 2, # 6 p. 357 - 365
反应条件
1: hydrogen; water / 160 °C / 30003 Torr / |Autoclave
2: sodium hydroxide / water / 10 h / |Reflux
3: hydrogen / 180 °C / 30003 Torr / |Autoclave
View Scheme
参考文献
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940
参考文献
Ghorpade, Sandeep R.; Bastawade, Kulbhushan B.; Gokhale, Digambar V.; Shinde, Popat D.; Mahajan, Vishal A.; Kalkote, Uttam R.; Ravindranathan
Tetrahedron Asymmetry, 1999 , vol. 10, # 21 p. 4115 - 4122
反应条件
in di-isopropyl ether
T=20°C;
参考文献
O'Byrne, Aisling; Murray, Cian; Keegan, Dearbhla; Palacio, Carole; Evans, Paul; Morgan, Ben S.
Organic and Biomolecular Chemistry, 2010 , vol. 8, # 3 p. 539 - 545
反应条件
1: hydrogen; water / 160 °C / 30003 Torr / |Autoclave
2: sodium hydroxide / water / 10 h / |Reflux
View Scheme
参考文献
Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie
Green Chemistry, 2013 , vol. 15, # 7 p. 1932 - 1940
反应条件
1.1: LDA / tetrahydrofuran; hexane / 0.33 h / -20 °C
1.2: 85 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C
2.1: imidazole / CH2Cl2 / 0.33 h / 0 °C
3.1: 4.00 g / N-iodosuccinimide; AgNO3 / acetone / 3.5 h / 0 °C
4.1: BH3*SMe2; cyclohexene / diethyl ether / 1 h / 0 °C
4.2: 82 percent / glacial AcOH / diethyl ether / 0.5 h / 0 °C
5.1: (1S)-(+)-10-camphorsulfonic acid / methanol / 2 h / 0 °C
5.2: 75 percent / MnO2 / CH2Cl2 / 14 h / 20 °C
View Scheme
参考文献
Tanaka, Hiroshi; Hasegawa, Tsuyoshi; Iwashima, Makoto; Iguchi, Kazuo; Takahashi, Takashi
Organic Letters, 2004 , vol. 6, # 7 p. 1103 - 1106
