3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel

Base Information

• Chemical Name: 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel
• CAS No.: 860782-61-2
• Molecular Formula: C₆₆H₈₉NO₁₅Si₂
• Molecular Weight: 1192.6
• Mol file: 860782-61-2.mol

Synonyms:3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel

Chemical Property of 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel

There total 13 articles about 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel 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: 65.0%

4-deacetyl-4-acryloyl-7-O-triethylsilylbaccatin III (172482-21-2) + (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one (360075-38-3) → 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel (860782-61-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 3h;

DOI:10.1021/jm061071x

Reference yield:

(3-allyloxy-benzylidene)-(4-methoxy-phenyl)-amine → 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel (860782-61-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / i-Pr₂NEt / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 48 percent / lipase PS / aq. phosphate buffer; acetonitrile / 74 h / 20 °C / pH 7

3: 99 percent / aq. KOH / tetrahydrofuran / 0.25 h

4: 1.15 g / imidazole / dimethylformamide / 8 h / 20 °C

5: 78 percent / aq. ceric ammonium nitrate / acetonitrile / 1.08 h / 0 °C

6: 82 percent / dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

7: 65 percent / lithium hexamethyldisilazide / tetrahydrofuran / 3 h / -40 °C

With 1H-imidazole; dmap; potassium hydroxide; ammonium cerium(IV) nitrate; Lipase PS; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm061071x

Reference yield:

4-deacetyl-4-acryloyl-10-deacetylbaccatin III (860782-20-3) → 3'-dephenyl-3'-(m-allyloxyphenyl)-4-deacetyl-4-acryloyl-7-O-triethylsilyl-2'-O-triisopropylsilylpaclitaxel (860782-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / CeCl₃ / tetrahydrofuran / 4 h

2: 72 percent / imidazole / CH₂Cl₂ / 3 h / 0 °C

3: 65 percent / lithium hexamethyldisilazide / tetrahydrofuran / 3 h / -40 °C

With 1H-imidazole; cerium(III) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm061071x

upstream raw materials:

4-deacetyl-4-acryloyl-7-O-triethylsilylbaccatin III

(3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

4-deacetyl-4-acryloyl-10-deacetylbaccatin III

4-deacetyl-4-acryloylbaccatin III

Downstream raw materials:

C₄₉H₅₁NO₁₅