4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate

Base Information

• Chemical Name: 4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
• CAS No.: 133524-70-6
• Molecular Formula: C40H47 N O13
• Molecular Weight: 749.812
• DSSTox Substance ID: DTXSID40928173
• Mol file: 133524-70-6.mol

Synonyms:SCHEMBL12316392;DTXSID40928173;4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate

Chemical Property of 4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 12
• Exact Mass: 749.30474055
• Heavy Atom Count: 54
• Complexity: 1550

Purity/Quality:

99.90% ^*data from raw 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)N)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@](C3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)N)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)OC(=O)C

Technology Process of 4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate

There total 21 articles about 4,10-Bis(acetyloxy)-13-[(3-amino-2-hydroxy-3-phenylpropanoyl)oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate 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: 94.0%

7-(triethylsilyl)baccatin III 13- (155399-27-2) → 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 5h; under 2585.7 Torr;

Reference yield: 90.0%

10-acetyldocetaxel (125354-16-7) → 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/S0968-0896(03)00181-0

Reference yield: 60.0%

3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel (602319-12-0) → 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6)

Guidance literature:

With acetic acid; zinc; In ethyl acetate; for 8h;

DOI:10.1021/jm049344g

upstream raw materials:

7-(triethylsilyl)baccatin III 13-

10-acetyldocetaxel

3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel

10-deacetylbaccatin III

Downstream raw materials:

N-(4-azidobenzoyl)-N-debenzoyltaxol

benzoyltaxol

7-(triethylsilyl)baccatin III 13-

C₄₇H₄₆⁽²⁾H₅NO₁₄

Refernces

• 1、 -. "Trifluoro isopropyl-substituted taxol derivatives, and applications thereof". . . Retrieved 2017/07/22.
• 2、 Nevarez, Danielle M.,Mengistu, Yemane A.,Nawarathne, Irosha N.,Walker, Kevin D.. "An N-aroyltransferase of the bahd superfamily has broad aroyl CoA specificity in vitro with analogues of N-dearoylpaclitaxel". experimental part. p. 5994 - 6002. Retrieved 2009/09/24.