4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

Base Information

Chemical Name:4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin
CAS No.:252192-02-2
Molecular Formula:C₃₂H₃₆O₁₁
Molecular Weight:596.631
Hs Code.:

Synonyms:4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

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Chemical Property of 4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

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Technology Process of 4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

There total 5 articles about 4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 34.0%

: 7486-35-3
tri-n-butyl(vinyl)tin

: 252191-99-4
4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylene-6,7-di-O-trifluoromethylsulfonyl-4-epipodophyllotoxin

: 252192-02-2
4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,6-di-tert-butyl-4-methyl-phenol; lithium chloride; In N,N-dimethyl-formamide; at 140 ℃; for 0.666667h;
DOI:10.1016/S0040-4020(99)00756-5

Reference yield:

: 33419-42-0
etoposide

: 252192-02-2
4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

2.1: BCl₃ / CH₂Cl₂ / -65 - -45 °C

2.2: aq. KHCO₃ / 0.5 h

2.3: 62 percent / CaCO₃ / H₂O / 0.5 h / Heating

3.1: 93 percent / 2,6-lutidine; 4-DMAP / CH₂Cl₂ / 2 h / -40 °C

4.1: 96 percent / Zn; AcOH / dioxane / 1 h / 80 °C

5.1: 34 percent / PdCl₂dppf; LiCl; 2,6-di-tert-butyl-4-methylphenol / dimethylformamide / 0.67 h / 140 °C

With pyridine; 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,6-di-tert-butyl-4-methyl-phenol; boron trichloride; acetic acid; lithium chloride; zinc; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Substitution / 2.2: Hydrolysis / 2.3: Substitution / 3.1: Substitution / 4.1: Substitution / 5.1: Stille vinylation;
DOI:10.1016/S0040-4020(99)00756-5

Reference yield:

: 4'-O-demethyl-4'-O-(2,2,2-trichloroethoxy)carbonyl-4-O-[4,6-O-ethylidene-2,3-di-O-(2,2,2-trichloroethoxy)carbonyl-β-D-glucopyranosyl]-4-epipodophyllotoxin

: 252192-02-2
4'-O-demethyl-4'-O-(4,6-O-ethylidene-β-D-glucopyranosyl)-6,7-di-O-demethylenedoxy-6,7-diethenyl-4-epipicropodophyllin

Guidance literature:: Multi-step reaction with 4 steps

1.1: BCl₃ / CH₂Cl₂ / -65 - -45 °C

1.2: aq. KHCO₃ / 0.5 h

1.3: 62 percent / CaCO₃ / H₂O / 0.5 h / Heating

2.1: 93 percent / 2,6-lutidine; 4-DMAP / CH₂Cl₂ / 2 h / -40 °C

3.1: 96 percent / Zn; AcOH / dioxane / 1 h / 80 °C

4.1: 34 percent / PdCl₂dppf; LiCl; 2,6-di-tert-butyl-4-methylphenol / dimethylformamide / 0.67 h / 140 °C

With 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,6-di-tert-butyl-4-methyl-phenol; boron trichloride; acetic acid; lithium chloride; zinc; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Hydrolysis / 1.3: Substitution / 2.1: Substitution / 3.1: Substitution / 4.1: Stille vinylation;
DOI:10.1016/S0040-4020(99)00756-5