[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯合成路线 (共 63 条)
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH2Cl2 / 3 h / Ambient temperature
2: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
3: 75 percent / pyridine / CH2Cl2 / -5 °C
4: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
6: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
7: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
9: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
10: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
11: 91 percent / pyridine / Ambient temperature
12: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
13: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
14: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
15: 53 percent / K2CO3 / methanol / 19 h / 100 °C
16: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
17: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
18: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
19: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
20: 70 percent / DMAP / 0.33 h / 40 °C
21: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
22: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
23: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
24: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
25: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
26: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
27: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
28: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
2: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
3: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
4: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
5: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
6: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
3: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
4: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
6: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
7: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
8: 91 percent / pyridine / Ambient temperature
9: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
10: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
11: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
12: 53 percent / K2CO3 / methanol / 19 h / 100 °C
13: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
14: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
15: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
16: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
17: 70 percent / DMAP / 0.33 h / 40 °C
18: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
19: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
20: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
21: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
22: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
23: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
24: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
25: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
2: 75 percent / pyridine / CH2Cl2 / -5 °C
3: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
5: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
6: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
8: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
9: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
10: 91 percent / pyridine / Ambient temperature
11: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
12: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
13: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
14: 53 percent / K2CO3 / methanol / 19 h / 100 °C
15: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
16: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
17: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
18: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
19: 70 percent / DMAP / 0.33 h / 40 °C
20: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
21: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
22: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
23: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
24: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
25: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
26: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
27: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
2: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
3: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
4: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
5: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
6: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
7: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
2: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C
3: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH2Cl2 / 3 h / Ambient temperature
4: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
5: 75 percent / pyridine / CH2Cl2 / -5 °C
6: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
8: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
9: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
11: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
12: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
13: 91 percent / pyridine / Ambient temperature
14: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
15: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
16: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
17: 53 percent / K2CO3 / methanol / 19 h / 100 °C
18: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
19: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
20: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
21: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
22: 70 percent / DMAP / 0.33 h / 40 °C
23: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
24: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
25: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
26: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
27: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
28: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
29: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
30: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 91 percent / pyridine / Ambient temperature
2: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
3: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
4: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
5: 53 percent / K2CO3 / methanol / 19 h / 100 °C
6: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
7: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
8: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
9: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
10: 70 percent / DMAP / 0.33 h / 40 °C
11: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
12: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
13: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
14: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
15: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
16: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
17: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
18: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
2: 53 percent / K2CO3 / methanol / 19 h / 100 °C
3: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
4: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
5: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
6: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
7: 70 percent / DMAP / 0.33 h / 40 °C
8: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
9: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
10: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
11: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
12: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
13: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
14: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
15: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 53 percent / K2CO3 / methanol / 19 h / 100 °C
2: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
3: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
4: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
5: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
6: 70 percent / DMAP / 0.33 h / 40 °C
7: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
8: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
9: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
10: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
11: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
12: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
13: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
14: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
2: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
3: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
4: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
5: 70 percent / DMAP / 0.33 h / 40 °C
6: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
7: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
8: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
9: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
10: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
11: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
12: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
13: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777