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ChemicalBook CAS DataBase List Milbemycin D
77855-81-3

Milbemycin D synthesis

9synthesis methods
-

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]

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