ChemicalBook CAS DataBase List Avermectin B1a

Avermectin B1a synthesis

8synthesis methods

Product Name:Avermectin B1a
CAS Number:65195-55-3
Molecular formula:C48H72O14
Molecular Weight:873.09

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

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Yield:-

Steps:

Multi-step reaction with 25 steps
1: 1.) Ph₃P; 2.) n-BuLi / 1.) CH₂Cl₂; 2.) THF
2: Me₃SiBr / CH₂Cl₂ / -30 °C
3: Et₃N, DMAP / CH₂Cl₂
4: 1.) n-BuLi, PPTS; 2.) H₂, pyridine; 3.) BF₃*Et₂O / 2.) Pd/BaSO₄-C / 1.) Et₂O, -78 deg C; 2.) EtOAc; 3.) THF
5: 87 percent / n-Bu₄NF / tetrahydrofuran
6: 85 percent / Ph₃P / tetrahydrofuran
7: 90 percent / m-CPBA / CH₂Cl₂ / -10 °C
8: 1.) n-BuLi; 2.) Na-Hg, KH₂PO₄ / 1.) THF, -78 deg C; 2.) MeOH, THF
9: 95 percent / n-Bu₄NF / tetrahydrofuran
10: 75 percent / Li/NH₃
11: 78 percent / Et₃N / CH₂Cl₂
12: 90 percent / imidazole, DMAP / dimethylformamide
13: 80 percent / NaOMe / methanol; CH₂Cl₂
14: 83 percent / n-Bu₃P / tetrahydrofuran
15: 96 percent / m-CPBA / CH₂Cl₂
16: 47 percent / n-BuLi / tetrahydrofuran / -78 °C
17: 1.) SOCl₂; 2.) Na-Hg / 1.) pyridine, methanol
18: 85 percent / n-Bu₄NF / tetrahydrofuran
19: 72 percent / KOH / H₂O; tetrahydrofuran
20: 30 percent / DCC, DMAP / CH₂Cl₂
21: 91 percent / imidazole / dimethylformamide
22: 72 percent / AgOTf / CH₂Cl₂; toluene
23: 96 percent / Et₃N, DMAP / CH₂Cl₂
24: 1.) LDA, Me₃SiCl; 2.) AcOH / 1.) THF, -78 deg C; 2.) THF, -78 deg C then r.t.
25: 90 percent / n-Bu₄NF / tetrahydrofuran