ChemicalBook CAS DataBase List Maytansine

Maytansine synthesis

5synthesis methods

Product Name:Maytansine
CAS Number:35846-53-8
Molecular formula:C34H46ClN3O10
Molecular Weight:692.2

Spiro[2-azabicyclo[16.3.1]docosa-1(22),6,13,15,18,20-hexaene-11,2'-[1,3]dithian]-3-one, 9-[(aminocarbonyl)oxy]-21-chloro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-12,20-dimethoxy-2,6,8,16-tetramethyl-, [5S-(5R*,6E,8R*,9R*,12S*,13E,15E)]- (9CI)

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Yield:-

Steps:

Multi-step reaction with 6 steps
1: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C
2: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C
3: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C
4: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C
5: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C
6: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C

References:

Corey;Weigel;Chamberlin;et al. [Journal of the American Chemical Society,1980,vol. 102,# 21,p. 6613 - 6615]