7-O-(Triethylsilyl) Paclitaxel synthesis

Yield:-

Steps:

Multi-step reaction with 37 steps
1.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C
2.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C
2.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C
2.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C
3.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C
4.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C
5.1: 90 percent / MeONa / methanol / 1 h / 0 °C
6.1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C
7.1: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C
8.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C
9.1: 90 percent / PDC / CH₂Cl₂ / 16 h / 20 °C
10.1: s-BuLi / cyclohexane / 0.42 h / -23 °C
10.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C
11.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C
12.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
13.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C
14.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂; acetonitrile / 1 h / 20 °C
15.1: 98 percent / PdCl₂; H₂O / dimethylformamide / 3.5 h / 20 °C
16.1: 71 percent / TiCl₂; LiAlH₄ / tetrahydrofuran / 0.33 h / 40 °C
17.1: Na; NH₃ / tetrahydrofuran / 2 h / -78 - -45 °C
18.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C
19.1: 100 percent / pyridine / CH₂Cl₂ / 1.17 h / -45 °C
20.1: 84 percent / DMAP / benzene / 10 h / 35 °C
21.1: HCl; H₂O / tetrahydrofuran / 10 h / 60 °C
22.1: pyridine / 0.67 h / 20 °C
23.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C
24.1: DMAP / 4 h / 100 °C
24.2: DMAP / toluene / 4 h / 100 °C
25.1: P(OMe)3 / 5 h / 110 °C
26.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C
27.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C
28.1: 98 percent / pyridine / 0.17 h / -23 °C
29.1: 15 percent / CuBr; PhCO₃(t-Bu) / acetonitrile / 13 h / -23 °C
30.1: 92 percent / OsO₄; pyridine / diethyl ether / 17 h / 20 °C
31.1: 42 percent / DBU / toluene / 1.75 h / 50 °C
32.1: 91 percent / DMAP; pyridine / 13 h / 20 °C
33.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C
34.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C
35.1: 87 percent / pyridine / 0.5 h / 20 °C
36.1: 66 percent / DPTC; DMAP / toluene / 4 h / 73 °C
37.1: 76 percent / H₂ / Pd(OH)2/C / ethanol / 23 h / 20 °C

References:

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]