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

Base Information

• Chemical Name: 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel
• CAS No.: 230283-83-7
• Molecular Formula: C₅₉H₇₈N₄O₁₅Si₂
• Molecular Weight: 1139.46
• Mol file: 230283-83-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel 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: 79.0%

3-azidobenzoic acid (1843-35-2) + 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-4-(methoxycarbonyl)-paclitaxel (230283-91-7) → 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel (230283-83-7)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In toluene; at 20 ℃; for 24h;

DOI:10.1016/S0968-0896(00)00233-9

Reference yield:

2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-1,2-carbonato-paclitaxel (160768-77-4) → 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel (230283-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hexamethyldisilamide / tetrahydrofuran / 0.25 h / -78 °C

2: 59 percent Turnov_. / LiOH / tetrahydrofuran; H₂O / 1.5 h / 20 °C

3: 79 percent / dicyclohexylcarbodiimide; 4-N-pyrrolidinopyridine / toluene / 24 h / 20 °C

With lithium hydroxide; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; water; toluene;

DOI:10.1016/S0968-0896(00)00233-9

Reference yield:

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate (225660-90-2) → 2'-O-tert-butyldimethylsilyl-7-O-triethylsilyl-2-debenzoyl-2-(3-azidobenzoyl)-4-deacetyl-4-(methoxycarbonyl)-paclitaxel (230283-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent Turnov_. / LiOH / tetrahydrofuran; H₂O / 1.5 h / 20 °C

2: 79 percent / dicyclohexylcarbodiimide; 4-N-pyrrolidinopyridine / toluene / 24 h / 20 °C

With lithium hydroxide; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; toluene;

DOI:10.1016/S0968-0896(00)00233-9

upstream raw materials:

3-azidobenzoic acid

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

2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-1,2-carbonato-paclitaxel

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