2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate

Base Information

• Chemical Name: 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate
• CAS No.: 225660-90-2
• Molecular Formula: C₅₃H₇₃NO₁₅Si₂
• Molecular Weight: 1020.33
• Mol file: 225660-90-2.mol

Synonyms:2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate

Chemical Property of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate

There total 3 articles about 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate 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:

triethylsilyl chloride (994-30-9) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate (225660-90-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) imidazole, 2.) imidazole / 1.) DMF, 60 deg C, 2 h, 2.) DMF, room temp., 1 h

2: 66 percent / Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

3: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

4: 1.) LHMDS / 1.) THF, -78 deg C (7 min), room temperature (1 min), 2.) THF, -78 deg C, 10 min

With 1H-imidazole; N-benzyl-trimethylammonium hydroxide; lithium hexamethyldisilazane; In methanol; dichloromethane;

DOI:10.1021/jo982095h

Reference yield:

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel (156413-61-5) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate (225660-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

2: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

3: 1.) LHMDS / 1.) THF, -78 deg C (7 min), room temperature (1 min), 2.) THF, -78 deg C, 10 min

With N-benzyl-trimethylammonium hydroxide; lithium hexamethyldisilazane; In methanol; dichloromethane;

DOI:10.1021/jo982095h

Reference yield:

2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel (160768-75-2) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate (225660-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

2: 1.) LHMDS / 1.) THF, -78 deg C (7 min), room temperature (1 min), 2.) THF, -78 deg C, 10 min

With lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jo982095h

upstream raw materials:

triethylsilyl chloride

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel

2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel

Downstream raw materials:

C₆₀H₈₁NO₁₅Si₂

2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel

2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-4-(methoxycarbonyl)-paclitaxel

2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel