4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

Base Information

• Chemical Name: 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin
• CAS No.: 118356-07-3
• Molecular Formula: C₂₇H₃₄O₈Si
• Molecular Weight: 514.648
• Mol file: 118356-07-3.mol

Synonyms:4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

Chemical Property of 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin

There total 2 articles about 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin 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: 89.0%

4'-demethylepipodophyllotoxin (6559-91-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin (118356-07-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2004.01.017

Reference yield:

podofilox (518-28-5) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin (118356-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HBr 2.) BaCO₃, H₂O / 1.) CH₂Cl₂, 0 deg C, 20 h 2.) acetone, 2 h

2: 60 percent / imidazole / tetrahydrofuran

With 1H-imidazole; water; hydrogen bromide; barium carbonate; In tetrahydrofuran;

DOI:10.1021/jm00123a016

Reference yield: 88.0%

4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-epipodophyllotoxin (118356-07-3) → 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-podophyllotoxone (491580-64-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.333333h;

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

upstream raw materials:

4'-demethylepipodophyllotoxin

tert-butyldimethylsilyl chloride

podofilox

Downstream raw materials:

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

8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-6,7-bis-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-ol

[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetonitrile

2-[(4aR,5R,6R,11bS)-6-(4-Hydroxy-3,5-dimethoxy-phenyl)-2,2-dimethyl-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthren-5-yl]-acetamide