ChemicalBook CAS DataBase List dolastatin 10

dolastatin 10 synthesis

13synthesis methods

Product Name:dolastatin 10
CAS Number:110417-88-4
Molecular formula:C42H68N6O6S
Molecular Weight:785.09

13139-16-7 Synthesis

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110417-88-4
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Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: N,N'-carbonyldiimidazole; magnesium chloride; triethylamine / tetrahydrofuran / 3 h / 20 °C
1.2: 88 percent / triethylamine; anhydrous magnesium chloride / tetrahydrofuran / 39 h / 20 °C
2.1: 100 percent / hydrogen chloride / ethanol / 2 h / 0 °C
3.1: hydrogen / [RuBr₂((R)-2,2'-(Ph₂P)2-6,6'-(MeO)2-1,1'-biphenyl)] / ethanol / 24 h / 50 °C / 9120.61 Torr
4.1: 74 percent / LiHMDS; HMPA / tetrahydrofuran / 0.42 h / -20 °C
5.1: 81 percent / aq. NaOH / ethanol / 16 h / 20 °C
6.1: 72 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 16 h / 0 - 20 °C
7.1: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C
8.1: 55 percent / ethyldiisopropylamine; tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 74 h / 0 - 20 °C
9.1: trifluoroacetic acid / CH₂Cl₂ / 4 h / 20 °C
10.1: 52 percent / N-methylmorpholine; diethyl phosphorocyanidate / dimethylformamide / 38 h / 0 °C

References:

Mordant, Céline;Reymond, Sébastien;Tone, Hitoshi;Lavergne, Damien;Touati, Ridha;Ben Hassine, Bechir;Ratovelomanana-Vidal, Virginie;Genet, Jean-Pierre [Tetrahedron,2007,vol. 63,# 27,p. 6115 - 6123]

69610-41-9 Synthesis