7,13-二-O-(三乙基硅烷基)浆果赤霉素III合成路线 （共 52 条）
反应条件
1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
2: 98 percent / pyridine / 0.17 h / -23 °C
3: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
4: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
5: 42 percent / DBU / toluene / 1.75 h / 50 °C
6: 91 percent / DMAP; pyridine / 13 h / 20 °C
7: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
2.1: DMAP / 4 h / 100 °C
2.2: DMAP / toluene / 4 h / 100 °C
3.1: P(OMe)3 / 5 h / 110 °C
4.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
5.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
6.1: 98 percent / pyridine / 0.17 h / -23 °C
7.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
8.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
9.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
10.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
11.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: DMAP / 4 h / 100 °C
1.2: DMAP / toluene / 4 h / 100 °C
2.1: P(OMe)3 / 5 h / 110 °C
3.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
4.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
5.1: 98 percent / pyridine / 0.17 h / -23 °C
6.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
7.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
8.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
9.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
10.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C
2.1: s-BuLi / cyclohexane / 0.42 h / -23 °C
2.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C
3.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C
4.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
5.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C
6.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C
7.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C
8.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C
9.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C
10.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C
11.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
12.1: 84 percent / DMAP / benzene / 10 h / 35 °C
13.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
14.1: pyridine / 0.67 h / 20 °C
15.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
16.1: DMAP / 4 h / 100 °C
16.2: DMAP / toluene / 4 h / 100 °C
17.1: P(OMe)3 / 5 h / 110 °C
18.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
19.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
20.1: 98 percent / pyridine / 0.17 h / -23 °C
21.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
22.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
23.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
24.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
25.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: s-BuLi / cyclohexane / 0.42 h / -23 °C
1.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C
2.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C
3.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
4.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C
5.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C
6.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C
7.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C
8.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C
9.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C
10.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
11.1: 84 percent / DMAP / benzene / 10 h / 35 °C
12.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
13.1: pyridine / 0.67 h / 20 °C
14.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
15.1: DMAP / 4 h / 100 °C
15.2: DMAP / toluene / 4 h / 100 °C
16.1: P(OMe)3 / 5 h / 110 °C
17.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
18.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
19.1: 98 percent / pyridine / 0.17 h / -23 °C
20.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
21.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
22.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
23.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
24.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 85 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 0.75 h / 20 °C
2.1: 91 percent / PdCl2; H2O / dimethylformamide / 4 h / 20 °C
3.1: 52 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.08 h / 35 °C
4.1: Na; NH3 / tetrahydrofuran / 0.75 h / -78 - -45 °C
5.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
6.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
7.1: 84 percent / DMAP / benzene / 10 h / 35 °C
8.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
9.1: pyridine / 0.67 h / 20 °C
10.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
11.1: DMAP / 4 h / 100 °C
11.2: DMAP / toluene / 4 h / 100 °C
12.1: P(OMe)3 / 5 h / 110 °C
13.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
14.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
15.1: 98 percent / pyridine / 0.17 h / -23 °C
16.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
17.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
18.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
19.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
20.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.67 h / -45 °C
2.1: 85 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 0.75 h / 20 °C
3.1: 91 percent / PdCl2; H2O / dimethylformamide / 4 h / 20 °C
4.1: 52 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.08 h / 35 °C
5.1: Na; NH3 / tetrahydrofuran / 0.75 h / -78 - -45 °C
6.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
7.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
8.1: 84 percent / DMAP / benzene / 10 h / 35 °C
9.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
10.1: pyridine / 0.67 h / 20 °C
11.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
12.1: DMAP / 4 h / 100 °C
12.2: DMAP / toluene / 4 h / 100 °C
13.1: P(OMe)3 / 5 h / 110 °C
14.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
15.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
16.1: 98 percent / pyridine / 0.17 h / -23 °C
17.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
18.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
19.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
20.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
21.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: Na; NH3 / tetrahydrofuran / 0.75 h / -78 - -45 °C
2.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
3.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
4.1: 84 percent / DMAP / benzene / 10 h / 35 °C
5.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
6.1: pyridine / 0.67 h / 20 °C
7.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
8.1: DMAP / 4 h / 100 °C
8.2: DMAP / toluene / 4 h / 100 °C
9.1: P(OMe)3 / 5 h / 110 °C
10.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
11.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
12.1: 98 percent / pyridine / 0.17 h / -23 °C
13.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
14.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
15.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
16.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
17.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 100 percent / CSA / CH2Cl2 / 1 h / 20 °C
2.1: 97 percent / DDQ; H2O / CH2Cl2 / 1 h / 20 °C
3.1: 90 percent / PDC / CH2Cl2 / 16 h / 20 °C
4.1: s-BuLi / cyclohexane / 0.42 h / -23 °C
4.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C
5.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C
6.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
7.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C
8.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 1 h / 20 °C
9.1: 98 percent / PdCl2; H2O / dimethylformamide / 3.5 h / 20 °C
10.1: 71 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.33 h / 40 °C
11.1: Na; NH3 / tetrahydrofuran / 2 h / -78 - -45 °C
12.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C
13.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
14.1: 84 percent / DMAP / benzene / 10 h / 35 °C
15.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
16.1: pyridine / 0.67 h / 20 °C
17.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
18.1: DMAP / 4 h / 100 °C
18.2: DMAP / toluene / 4 h / 100 °C
19.1: P(OMe)3 / 5 h / 110 °C
20.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
21.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
22.1: 98 percent / pyridine / 0.17 h / -23 °C
23.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
24.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
25.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
26.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
27.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
反应条件
1.1: 91 percent / PdCl2; H2O / dimethylformamide / 4 h / 20 °C
2.1: 52 percent / TiCl2; LiAlH4 / tetrahydrofuran / 0.08 h / 35 °C
3.1: Na; NH3 / tetrahydrofuran / 0.75 h / -78 - -45 °C
4.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
5.1: 100 percent / pyridine / CH2Cl2 / 1.17 h / -45 °C
6.1: 84 percent / DMAP / benzene / 10 h / 35 °C
7.1: HCl; H2O / tetrahydrofuran / 10 h / 60 °C
8.1: pyridine / 0.67 h / 20 °C
9.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C
10.1: DMAP / 4 h / 100 °C
10.2: DMAP / toluene / 4 h / 100 °C
11.1: P(OMe)3 / 5 h / 110 °C
12.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
13.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
14.1: 98 percent / pyridine / 0.17 h / -23 °C
15.1: 15 percent / CuBr; PhCO3(t-Bu) / acetonitrile / 13 h / -23 °C
16.1: 92 percent / OsO4; pyridine / diethyl ether / 17 h / 20 °C
17.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
18.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
19.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
View Scheme
参考文献
Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-Ichirou; Hasegawa, Masatoshi; Yamada, Koji; Saitoh, Katsuyuki
Chemistry - A European Journal, 1999 , vol. 5, # 1 p. 121 - 161
