PACLITAXEL SIDE CHAIN NO 1

Base Information

• Chemical Name: PACLITAXEL SIDE CHAIN NO 1
• CAS No.: 133066-61-2
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• Mol file: 133066-61-2.mol

Synonyms:PACLITAXEL SIDE CHAIN NO 1;(3R,4S)-1-BENZOYL-3-[(TRIETHYLSILY)OXY]-4-PHENYL-2-AZETIDINONE;(3R,4S)-1-BENZOYL-3-(2-ETHOXYETHOXY)-4-PHENYL-2-AZETIDIONE

Chemical Property of PACLITAXEL SIDE CHAIN NO 1

Chemical Property:

• Boiling Point: 464.832 °C at 760 mmHg
• Flash Point: 234.922 °C
• PSA: 55.84000
• Density: 1.227g/cm³
• LogP: 3.11590

Purity/Quality:

99% ^*data from raw suppliers

1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PACLITAXEL SIDE CHAIN NO 1

There total 7 articles about PACLITAXEL SIDE CHAIN NO 1 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: 92.0%

benzoyl chloride (98-88-4) + (3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone (201856-48-6) → (3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone (201856-53-3,133066-61-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1016/S0040-4020(01)91210-4

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + benzoyl chloride (98-88-4) + (3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) + (3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone (201856-48-6) + ethyl vinyl ether (109-92-2,25104-37-4) → (3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone (201856-53-3,133066-61-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

Reference yield:

N-benzylidene-1,1,1-trimethylsilanamine (17599-61-0) → (3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone (201856-53-3,133066-61-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1. diisopropylamine, n-butyllithium / 1. THF, 2 h; 2. THF a.) -78 deg C, 4 h, b.) r.t.

2: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.42 h / Ambient temperature

3: 100 percent / tetrahydrofuran / 2 h / 0 °C

4: 92 percent / DMAP, triethylamine / CH₂Cl₂ / 2 h / 25 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)91210-4

upstream raw materials:

benzoyl chloride

(3R,4S)-3-<((R^*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

N-benzylidene-1,1,1-trimethylsilanamine

benzaldehyde

Downstream raw materials:

C₅₁H₅₇NO₁₃

9(R)-dihydrotaxol 7,9-acetonide

9(R)-dihydrotaxol

2'-EE-10-Deacetyl-7,10-bis(trichloroethoxycarbonyl)-taxol

Refernces

• 1、 -. "Method for preparation of taxol using β-lactam". . . Retrieved 2008/06/13.
• 2、 -. "Method for preparation of taxol using an oxazinone". . . Retrieved 2008/06/13.