4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin

Base Information

• Chemical Name: 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin
• CAS No.: 491580-65-5
• Molecular Formula: C₂₈H₃₄O₇Si
• Molecular Weight: 510.659
• Mol file: 491580-65-5.mol

Synonyms:4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin

Chemical Property of 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin

There total 4 articles about 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-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: 73.0%

diiodomethane (75-11-6) + 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-podophyllotoxone (491580-64-4) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin (491580-65-5)

Guidance literature:

diiodomethane; With zinc; In tetrahydrofuran; at 20 ℃; for 0.5h;

With titanium tetrachloride; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;

4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-podophyllotoxone; In tetrahydrofuran; dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/S0968-0896(02)00255-9

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin (491580-65-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; Dess-Martin periodane; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation / 3.3: Takai olefination;

DOI:10.1016/S0968-0896(02)00255-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin (491580-65-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; Dess-Martin periodane; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Dess-Martin oxidation / 3.3: Takai olefination;

DOI:10.1016/S0968-0896(02)00255-9

upstream raw materials:

diiodomethane

4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-podophyllotoxone

4'-demethylepipodophyllotoxin

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₂₈H₃₄O₈Si

5-[4-(tert-butyl-dimethyl-silanyloxy)-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

(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

(5R,5aR,8aR,9S)-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