[(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: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
3: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
4: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
5: 91 percent / pyridine / Ambient temperature
6: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
7: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
8: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
9: 53 percent / K2CO3 / methanol / 19 h / 100 °C
10: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
11: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
12: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
13: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
14: 70 percent / DMAP / 0.33 h / 40 °C
15: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
16: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
17: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
18: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
19: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
20: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
21: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
22: 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: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
2: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
4: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
5: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
6: 91 percent / pyridine / Ambient temperature
7: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
8: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
9: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
10: 53 percent / K2CO3 / methanol / 19 h / 100 °C
11: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
12: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
13: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
14: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
15: 70 percent / DMAP / 0.33 h / 40 °C
16: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
17: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
18: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
19: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
20: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
21: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
22: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
23: 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: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
2: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
3: 53 percent / K2CO3 / methanol / 19 h / 100 °C
4: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
5: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
6: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
7: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
8: 70 percent / DMAP / 0.33 h / 40 °C
9: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
10: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
11: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
12: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
13: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
14: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
15: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
16: 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: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
2: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
3: 91 percent / pyridine / Ambient temperature
4: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
5: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
6: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
7: 53 percent / K2CO3 / methanol / 19 h / 100 °C
8: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
9: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
10: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
11: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
12: 70 percent / DMAP / 0.33 h / 40 °C
13: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
14: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
15: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
16: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
17: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
18: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
19: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
20: 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: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
2: 70 percent / DMAP / 0.33 h / 40 °C
3: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
4: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
5: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
6: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
7: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
8: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
9: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
10: 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: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
2: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
3: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
4: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
5: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
6: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
7: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
8: 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: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
2: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
3: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
4: 70 percent / DMAP / 0.33 h / 40 °C
5: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
6: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
7: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
8: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
9: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
10: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
11: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
12: 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: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
2: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
3: 70 percent / DMAP / 0.33 h / 40 °C
4: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
5: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
6: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
7: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
8: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
9: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
10: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
11: 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
3: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C
4: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH2Cl2 / 3 h / Ambient temperature
5: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
6: 75 percent / pyridine / CH2Cl2 / -5 °C
7: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
9: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
10: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
12: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
13: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
14: 91 percent / pyridine / Ambient temperature
15: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
16: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
17: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
18: 53 percent / K2CO3 / methanol / 19 h / 100 °C
19: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
20: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
21: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
22: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
23: 70 percent / DMAP / 0.33 h / 40 °C
24: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
25: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
26: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
27: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
28: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
29: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
30: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
31: 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: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C
2: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH2Cl2 / 3 h / Ambient temperature
3: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
4: 75 percent / pyridine / CH2Cl2 / -5 °C
5: 87 percent / sodium methoxide / CH2Cl2; methanol / 0.67 h / 0 °C
7: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating
8: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C
10: 68 percent / n-Bu3SnH, AIBN / toluene / 0.58 h / Heating
11: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C
12: 91 percent / pyridine / Ambient temperature
13: 85 percent / triethylamine / CH2Cl2 / 0.5 h / Ambient temperature
14: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C
15: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH2Cl2, -10 deg C, 20 min 2.) -10 deg C, 5 min
16: 53 percent / K2CO3 / methanol / 19 h / 100 °C
17: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature
18: 85 percent / methanesulfonyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C
19: 90 percent / NaBH4 / propan-2-ol; CHCl3 / 0.67 h / Ambient temperature
20: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature
21: 70 percent / DMAP / 0.33 h / 40 °C
22: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature
23: 55 percent / n-Bu3SnH, AIBN / toluene / 0.5 h / Heating
24: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight
25: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
26: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
27: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
28: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
29: 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