4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

Base Information

Chemical Name:4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin
CAS No.:491580-73-5
Molecular Formula:C₃₀H₂₈O₁₀
Molecular Weight:548.546
Hs Code.:

Synonyms:4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

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Chemical Property of 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

Chemical Property:

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Technology Process of 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

There total 6 articles about 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin 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: 94.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 491580-71-3
(5R,5aR,8aR,9R)-5-(4-Hydroxy-3,5-dimethoxy-phenyl)-9-hydroxymethyl-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

: 491580-73-5
4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1016/S0968-0896(02)00255-9

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 491580-73-5
4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / imidazole / dimethylformamide / 4.5 h

2.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

3.1: zinc / tetrahydrofuran / 0.5 h / 20 °C

3.2: TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

3.3: 73 percent / tetrahydrofuran; CH₂Cl₂ / 20 h / 20 °C

4.1: BH₃/Me₂S / tetrahydrofuran / 2 h

4.2: 82 percent / H₂O₂; aq. phosphate buffer / tetrahydrofuran; methanol / 1.5 h / pH 7

5.1: pyridinium para-toluenesulfonate / aq. ethanol / 17 h / Heating

6.1: 94 percent / triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

With 1H-imidazole; dimethylsulfide; borane; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation / 3.3: Takai olefination;
DOI:10.1016/S0968-0896(02)00255-9

Reference yield:

: 118356-07-3
4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

: 491580-73-5
4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

2.1: zinc / tetrahydrofuran / 0.5 h / 20 °C

2.2: TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

2.3: 73 percent / tetrahydrofuran; CH₂Cl₂ / 20 h / 20 °C

3.1: BH₃/Me₂S / tetrahydrofuran / 2 h

3.2: 82 percent / H₂O₂; aq. phosphate buffer / tetrahydrofuran; methanol / 1.5 h / pH 7

4.1: pyridinium para-toluenesulfonate / aq. ethanol / 17 h / Heating

5.1: 94 percent / triethylamine / CH₂Cl₂ / 0.75 h / 0 °C

With dimethylsulfide; borane; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Dess-Martin oxidation / 2.3: Takai olefination;
DOI:10.1016/S0968-0896(02)00255-9