4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

Base Information

• Chemical Name: 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin
• CAS No.: 845863-32-3
• Molecular Formula: C₂₇H₃₄O₈Si
• Molecular Weight: 514.648
• Mol file: 845863-32-3.mol

Synonyms:4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

Chemical Property of 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

There total 1 articles about 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin 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:

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol (153230-77-4) → 4'-demethylepipodophyllotoxin (6559-91-7) + 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin (845863-32-3)

Guidance literature:

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol; With molecular sieve; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; for 2h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.333333h;

DOI:10.1021/jm0495733

Reference yield: 80.0%

4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin (845863-32-3) → 11-oxo-13-deoxo-4'-demethylepipodophyllotoxin (642409-76-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 23h;

DOI:10.1021/jm0495733

Reference yield:

4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin (845863-32-3) → (2-Amino-ethyl)-carbamic acid (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 h

2: 82 percent / Et₃N / CH₂Cl₂

3: 97 percent / pyridine / CH₂Cl₂ / 20 °C

4: 76 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

5: 65 percent / H₂ / Pd/C / ethyl acetate / 3 h

With pyridine; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm0495733

upstream raw materials:

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

Downstream raw materials:

11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin

11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-(formylmethyl)-4-desoxypodophyllotoxin

11-oxo-13-deoxo-4'-demethyl-4'-benzyloxycarbonyl-4β-allyl-4-desoxypodophyllotoxin