ChemicalBook CAS DataBase List 7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III

7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III synthesis

15synthesis methods

Product Name:7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III
CAS Number:103150-33-0
Molecular formula:C34H39Cl3O13
Molecular Weight:762.02

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III

103150-33-0
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$135.00/5mg

Yield:-

Steps:

Multi-step reaction with 20 steps
1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C
2.1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.08 h / 20 °C
3.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C
3.2: 89 percent / tetrahydrofuran / 1 h / -78 °C
4.1: 91 percent / tetrakis(triphenylphosphine)palladium / diethyl ether; tetrahydrofuran / 1 h / 20 °C
5.1: 88 percent / N-chlorosuccinimide / methanol / 10 h / 20 °C
6.1: 89 percent / pyridinium p-toluenesulfonate; 2-methoxypropene / CH₂Cl₂ / 0.05 h / 20 °C
7.1: 80 percent / lithium diisopropyl amide; MoO₅*pyridine*HMPA / tetrahydrofuran / 0.92 h / -23 °C
8.1: 92 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C
9.1: 68 percent / DBN / toluene / 10 h / Heating
10.1: 86 percent / OsO₄; pyridine / diethyl ether; tetrahydrofuran / 18 h / 20 °C
11.1: 86 percent / DBU / toluene / 4 h / Heating
12.1: pyridinium p-toluenesulfonic acid / methanol / 0.5 h / 20 °C
13.1: 15 mg / DMAP; imidazole / dimethylformamide / 5 h / 20 °C
14.1: 97 percent / H₂ / Pd(OH)2 / ethanol / 1 h / 20 °C
15.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / -78 - 0 °C
16.1: 66 percent / DMAP / CH₂Cl₂ / 6 h / 20 °C
17.1: 83 percent / tetrahydrofuran / 0.33 h / -78 °C
18.1: 88 percent / HF*pyridine / tetrahydrofuran / 2 h / 20 °C
19.1: 94 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C
20.1: 80 percent / TASF / tetrahydrofuran / 48 h / 20 °C

References:

Kusama, Hiroyuki;Hara, Ryoma;Kawahara, Shigeru;Nishimori, Toshiyuki;Kashima, Hajime;Nakamura, Nobuhito;Morihira, Koichiro;Kuwajima, Isao [Journal of the American Chemical Society,2000,vol. 122,# 16,p. 3811 - 3820]