ChemicalBook CAS DataBase List Milbemycin D

Milbemycin D synthesis

9synthesis methods

Product Name:Milbemycin D
CAS Number:77855-81-3
Molecular formula:C33H48O7
Molecular Weight:556.73

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

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Yield:-

Steps:

Multi-step reaction with 11 steps
1: 80 percent / Pr₄NRuO₄, NMO, 4 Angstroem molecular sieves / CH₂Cl₂
2: 61 percent / NaClO₂, 2-methyl-2-butene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 4 h / Ambient temperature
3: 63 percent / tetrabutylammonium fluoride / tetrahydrofuran / 96 h / Ambient temperature
4: 53 percent / N,N-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine, HCl / CHCl₃ / Heating
5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature
6: 79 percent / Pr₄NRuO₄, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature
7: Et₃N / CH₂Cl₂ / 8 h / 0 °C
8: 0.023 g / CH₂Cl₂ / 1 h / -78 °C
9: 66 percent / aq. 48percent HF, pyridine / acetonitrile / 24 h / Ambient temperature
10: NaIO₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature
11: 32 percent / NaBH₄ / methanol / 0.17 h / 0 °C

References:

Crimmins, Michael T.;Al-awar, Rima S.;Vallin, Isabelle M.;Hollis Jr., W. Gary;O'Mahony, Rosemary;Lever, John G.;Bankaitis-Davis, Danute M. [Journal of the American Chemical Society,1996,vol. 118,# 32,p. 7513 - 7528]