4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel

Base Information

• Chemical Name: 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel
• CAS No.: 817207-98-0
• Molecular Formula: C₇₂H₉₅NO₁₅Si₂
• Molecular Weight: 1270.71
• Mol file: 817207-98-0.mol

Synonyms:4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel

Chemical Property of 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel

There total 6 articles about 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-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: 57.0%

4-deacetyl-4-(pent-4-enoyl)-7-O-triethylsilylbaccatin III (360075-40-7) + (3R,4S)-1-benzoyl-4-(3-(benzyloxy)phenyl)-3-TIPS-azetidin-2-one (817207-78-6) → 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel (817207-98-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2004.09.002

Reference yield:

triisopropylsilyl chloride (13154-24-0) → 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel (817207-98-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 96 percent / CAN / acetonitrile; H₂O / 0.75 h / 0 °C

3: 90 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

4: 57 percent / NaH / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.09.002

Reference yield:

3-Benzyloxybenzaldehyde (1700-37-4) → 4-deacetyl-4-(4-pentanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel (817207-98-0)

Guidance literature:

Multi-step reaction with 8 steps

1: MgSO₄ / 1,2-dichloro-ethane / 20 °C

2: 25.1 g / triethylamine / 1,2-dichloro-ethane / -78 - 20 °C

3: 48 percent / lipase PS₃₀ / acetonitrile; aq. phosphate buffer / 168 h / 20 °C

4: 92 percent / KOH / tetrahydrofuran / 0.75 h / 0 °C

5: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

6: 96 percent / CAN / acetonitrile; H₂O / 0.75 h / 0 °C

7: 90 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

8: 57 percent / NaH / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; ammonium cerium(IV) nitrate; lipase PS₃₀; sodium hydride; magnesium sulfate; triethylamine; In tetrahydrofuran; phosphate buffer; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.09.002

upstream raw materials:

4-deacetyl-4-(pent-4-enoyl)-7-O-triethylsilylbaccatin III

(3R,4S)-1-benzoyl-4-(3-(benzyloxy)phenyl)-3-TIPS-azetidin-2-one

triisopropylsilyl chloride

3-Benzyloxybenzaldehyde

Downstream raw materials:

4-deacetyl-4-(3-carboxypropanoyl)-3'-desphenyl-3'-(m-benzyloxyphenyl)-7-TES-2'-TIPS-paclitaxel