2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel

Base Information

• Chemical Name: 2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel
• CAS No.: 165065-02-1
• Molecular Formula: C₅₃H₆₃NO₁₃Si
• Molecular Weight: 950.168
• Mol file: 165065-02-1.mol

Synonyms:2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel;165065-02-1;[(1S,2S,3R,4S,7R,10R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadeca-8,13-dien-2-yl] benzoate

Chemical Property of 2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel

Chemical Property:

• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 17
• Exact Mass: 949.40686760
• Heavy Atom Count: 68
• Complexity: 2020

Purity/Quality:

98%Min ^*data from raw suppliers

2''-O-(tert-Butyldimethylsilyl)-6,7-dehydroPaclitaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(C=CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O[Si](C)(C)C(C)(C)C)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3(C=C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O[Si](C)(C)C(C)(C)C)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)C)OC(=O)C

Technology Process of 2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel

There total 5 articles about 2'-O-(tert-Butyldimethylsilyl)-6,7-dehydropaclitaxel 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: 86.0%

2'-O-(t-butyldimethylsilyl)-7β-O-trifluoromethanesulfonyl-paclitaxel (165065-01-0) → Δ6,7-paclitaxel (158830-49-0) + 2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel (165065-02-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 40 ℃; for 4h;

DOI:10.1016/S0040-4020(97)00074-4

Reference yield:

taxol (33069-62-4) → 2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel (165065-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / imidazole / dimethylformamide

2: 1.) Tf₂O, 2.) DBU / 1.) pyridine, 25 deg C, 2.) 25 deg C

With 1H-imidazole; trifluoromethylsulfonic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00337-5

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel (165065-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / imidazole / dimethylformamide

2: 1.) Tf₂O, 2.) DBU / 1.) pyridine, 25 deg C, 2.) 25 deg C

With 1H-imidazole; trifluoromethylsulfonic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00337-5

upstream raw materials:

2'-O-(t-butyldimethylsilyl)-7β-O-trifluoromethanesulfonyl-paclitaxel

2'-O-(tert-butyldimethylsilyl)paclitaxel

taxol

tert-butyldimethylsilyl chloride

Downstream raw materials:

Δ^6,7-paclitaxel

2'-O-(tert-butyldimethylsilyl)-6α-hydroxy-7-epipaclitaxel

C₆₀H₇₁NO₁₇SSi

2'-O-(tert-butyldimethylsilyl)-6α-trifluoromethanesulfuryl-7-epipaclitaxel

Refernces

• 1、 Wender, Paul A.,Lee, Daesung,Lal, Tapan K.,Horwitz, Susan B.,Rao, Srinivasa. "Synthesis of novel taxol analogs and evaluation of their biological activities". . p. 1941 - 1944. Retrieved 2007/10/03.