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ChemicalBook CAS DataBase List ERYTHROMYCIN B

ERYTHROMYCIN B synthesis

8synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 14 steps
1.1: 69 percent / BF3*OEt2 / CH2Cl2 / 5 h / -78 °C
2.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH2Cl2 / 0.5 h / 20 °C
3.1: ozone; pyridine; Sudan III / CH2Cl2 / -78 °C
3.2: 85 percent / triphenylphosphine / CH2Cl2 / 2 h / 20 °C
4.1: 100 percent / Na2HPO4; m-CPBA / tetrahydrofuran; H2O / 15 h / 20 °C
5.1: 99 percent / hydrogen / palladium on charcoal / methanol; tetrahydrofuran / 3.5 h / 20 °C
6.1: 93 percent / 4-dimethylaminopyridine; triethylamine; 2,3,4-trichlorobenzoyl chloride / toluene / 0.25 h / 20 °C
7.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 28 h / 60 °C
8.1: 70 percent / KH2PO4; aq. HCl / tetrahydrofuran / 14 h / 50 °C
9.1: 61 percent / silver triflate; molecular sieves 4 Angstroem / CH2Cl2; toluene / 1 h / 0 °C
10.1: 40 percent / copper(II) oxide; molecular sieves 4 Angstroem; copper(II) trifluoromethanesulfonate / acetonitrile / 2 h / 20 °C
11.1: acetic acid; water / 14 h / 35 °C
12.1: 8.7 mg / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C
13.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH2Cl2 / 14 h / 20 °C
14.1: 95 percent / aq. MeOH / 8 h / Heating

References:

Breton, Philippe;Hergenrother, Paul J.;Hida, Tsuneaki;Hodgson, Anne;Judd, Andrew S.;Kraynack, Erica;Kym, Philip R.;Lee, Wen-Cherng;Loft, Michael S.;Yamashita, Masayuki;Martin, Stephen F. [Tetrahedron,2007,vol. 63,# 26,p. 5709 - 5729]

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