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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
L-羟基脯氨酸
合成路线
（共 225 条）
51-35-4
L-羟基脯氨酸
→
反应条件
83623-78-3
(4S)-1-boc-4-苄基-l-脯氨酸
反应条件
1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 6.2: 70 percent / tetrahydrofuran / 20 °C 7.1: 95 percent / Raney-Ni; hydrogen / methanol / 18 h / 20 °C / 760 Torr 8.1: TBAF / tetrahydrofuran / 6 h / 20 °C 8.2: NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme
参考文献
Del Valle, Juan R.; Goodman, Murray
Journal of Organic Chemistry, 2003 , vol. 68, # 10 p. 3923 - 3931
51-35-4
L-羟基脯氨酸
→
反应条件
40499-83-0
3-吡咯烷醇
反应条件
cyclohexenon in various solvent(s) T=154°C; 2 h;
参考文献
Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi
Chemistry Letters, 1986 , p. 893 - 896
51-35-4
L-羟基脯氨酸
→
反应条件
88043-21-4
N-Boc-反式-4-对甲苯磺酰氧基-L-脯氨酸甲酯
反应条件
1: thionyl chloride / methanol / 15 h / 0 - 20 °C 2: triethylamine / acetonitrile / 0 - 20 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 52, # 36 p. 9539 - 9543
Angew. Chem., , vol. 125, # 36 p. 9718 - 9722
51-35-4
L-羟基脯氨酸
→
反应条件
232931-57-6
SJG 136
反应条件
1: 87 percent / 4 M NaOH / tetrahydrofuran; H2O / 1 h / 0 °C / pH 9 2: 43 percent / H2SO4 / 2 h / Heating 3: 99 percent / LiBH4 / tetrahydrofuran / 2.5 h / 0 - 20 °C 4: 52 percent / Et3N; DBU / CH2Cl2 / 16 h / 20 °C 5: 95 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1.5 h / -70 °C 6: 87 percent / tetrahydrofuran / 2 h / 0 °C 7: 77 percent / PdCl2(PPh3)2; Bu3SnH / H2O; CH2Cl2 / 16 h / 20 °C 8: Et3N / tetrahydrofuran; H2O / 2 h / 20 °C 9: 94 percent / TBAF / tetrahydrofuran / 0.5 h / 0 - 20 °C 10: 61 percent / SnCl2*2H2O / methanol / 0.75 h / Heating 11: 50 percent / pyridine / CH2Cl2 / 2.5 h / 20 °C 12: 32 percent / NMO; 4 Angstroem molecular sieves; TPAP / CH2Cl2; acetonitrile / 2.5 h / 20 °C 13: 77 percent / PPh3; pyrrolidine; Pd(PPh3)4 / CH2Cl2; acetonitrile / 2.25 h / 20 °C View Scheme
参考文献
Gregson; Howard; Hartley; Brooks; Adams; Jenkins; Kelland; Thurston
Journal of Medicinal Chemistry, 2001 , vol. 44, # 5 p. 737 - 748
51-35-4
L-羟基脯氨酸
→
反应条件
96036-03-2
美罗培南
反应条件
1.1: sodium hydroxide / water / 0 - 5 °C 1.2: 0 - 5 °C 1.3: 0 - 5 °C 2.1: triethylamine; isopropyloxycarbonylchloride / dichloromethane / -30 - -20 °C 3.1: triethylamine / dichloromethane / -20 °C 4.1: N,N-dimethyl-formamide / 70 - 80 °C 5.1: sodium hydroxide; water / methanol / 5 - 10 °C 5.2: pH 2 6.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / -25 °C 7.1: hydrogen / palladium on activated charcoal / ethyl acetate; water / 3-(N-morpholino)propanesulfonic acid buffer View Scheme
参考文献
ORCHID CHEMICALS AND PHARMACEUTICALS LIMITED; KARALE, Sanjay Nivrutti; JANGALE, Arvind Atamaram; KALDATE, Ram Dattatraya
Patent: WO2011/141847 A1, 2011 ;
→
反应条件
88050-17-3
Fmoc-L-4-羟基脯氨酸
反应条件
sodium hydrogencarbonate in 1,4-dioxane; water; toluene
参考文献
ISIS Pharmaceuticals, Inc.
Patent: US6828427 B1, 2004 ;
Title/Abstract Full Text Show Details
ISIS Pharmaceuticals, Inc.
Patent: US6184389 B2, 2001 ;
28920-43-6
氯甲酸-9-芴基甲酯
+
51-35-4
L-羟基脯氨酸
→
反应条件
88050-17-3
Fmoc-L-4-羟基脯氨酸
反应条件
sodium hydrogencarbonate in 1,4-dioxane; water Yield given;
参考文献
Loenarz, Christoph; Mecinovic, Jasmin; Chowdhury, Rasheduzzaman; McNeill, Luke A.; Flashman, Emily; Schofield, Christopher J.
Angewandte Chemie - International Edition, 2009 , vol. 48, # 10 p. 1784 - 1787
51-35-4
L-羟基脯氨酸
→
反应条件
83623-93-2
顺式-1-N-BOC-4-甲氧基-L-脯氨酸
反应条件
1.1: thionyl chloride / 16 h / Heating 1.2: 96 percent / triethylamine / CH2Cl2 / 17 h 2.1: triphenylphosphine; DIAD / tetrahydrofuran / 1.5 h / 0 °C 3.1: 358 mg / sodium azide / methanol / 18 h / 40 °C 4.1: 48 percent / sodium hydride; 18-crown-6 / various solvent(s); tetrahydrofuran / 18 h / 20 °C 5.1: 84 percent / lithium hydroxide / methanol; H2O / 16 h / 20 °C View Scheme
参考文献
Taylor, Carol M.; Hardre, Renaud; Edwards, Patrick J. B.
Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1306 - 1315
25112-78-1
+
51-35-4
L-羟基脯氨酸
→
反应条件
33879-04-8
(+)-六氢-3a-羟基-7a-甲基-1H-茚-1,5(6H)-二酮
反应条件
in isopropyl alcohol
参考文献
Hoffmann-La Roche Inc.
Patent: US3975440 A1, 1976 ;
51-35-4
L-羟基脯氨酸
+
4457-32-3
氯甲酸对硝基苄酯
→
反应条件
96034-57-0
1,2-二羧基吡咯烷酸,4-羟基-1-[(4-硝基苯基)甲基]酯
反应条件
sodium hydroxide in dichloromethane T=0°C; Acylation; 2 h;
参考文献
Kang, Yong Koo; Shin, Kye Jung; Yoo, Kyung Ho; Seo, Kyung Jae; Hong, Chang Yong; Lee, Chang-Seok; Park, Seung Yong; Kim, Dong Jin; Park, Sang Woo
Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 2 p. 95 - 99
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