7,10-Dimethoxy-10-DAB III

Base Information

• Chemical Name: 7,10-Dimethoxy-10-DAB III
• CAS No.: 183133-94-0
• Molecular Formula: C31H40O10
• Molecular Weight: 572.653
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID301098192
• Mol file: 183133-94-0.mol

Synonyms:7,10-Dimethoxy-10-DAB III;183133-94-0;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-9,11-dihydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,15-dihydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;Cabazitaxel Impurity;10-Deacetyl-7,10-dimethylbaccatin III;7,10-Dimethoxy-10-deacetylbaccatin III;SCHEMBL7509209;7,10-Dimethoxy-10-DABIII;DTXSID301098192;BCP06123;EX-A3599;MFCD23100710;AKOS025401902;AC-27007;DS-12027;CS-0022604;F12858;A880845

Chemical Property of 7,10-Dimethoxy-10-DAB III

Chemical Property:

• Boiling Point: 675.8±55.0 °C(Predicted)
• PKA: 12.82±0.70(Predicted)
• PSA: 137.82000
• Density: 1.31
• LogP: 2.39000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMF (Slightly, Heated, Sonicated), DMSO (Very Slightly, Heated), Methanol and Wa
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 572.26214747
• Heavy Atom Count: 41
• Complexity: 1120

Purity/Quality:

10-Deacetyl-7,10-dimethoxy-Baccatin III ^*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)(CC1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)OC)C)OC
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)OC)C)OC
• Description: Cabazitaxel is a kind of Second line Drug for the treatment of prostate cancer, FDA Priority Review status approval listing is obtained because its curative effect is remarkable, for the advanced prostate cancer patients to the invalid even aggravation of Docetaxel, the first-selected medicine being used for the treatment of late period, hormone antagonist type prostate cancer.7,10-dimethoxy-10-Dab III is the important intermediate preparing Cabazitaxel.
• Uses: 4-Deacetyl-4-propionyl Cabazitaxel is an impurity of Cabazitaxel (C046500).A novel semi-synthetic taxane with antitumor activity used for the treatment of castration-resistant prostate cancer. A microtubule inhibitor.

Technology Process of 7,10-Dimethoxy-10-DAB III

There total 27 articles about 7,10-Dimethoxy-10-DAB III 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: 89.6%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + carbonic acid dimethyl ester (616-38-6) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0)

Guidance literature:

With dmap; caesium bromide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at -30 ℃; for 3h; Temperature; Reagent/catalyst;

Reference yield: 87.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + methyl trifluoromethanesulfonate (333-27-7) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0)

Guidance literature:

10-deacetylbaccatin III; With lithium hexamethyldisilazane; In tetrahydrofuran; at -72 ℃; for 0.666667h; Inert atmosphere;

methyl trifluoromethanesulfonate; In tetrahydrofuran; at -72 ℃; for 4.08333h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.11.037

Reference yield: 61.0%

7,10-methylthiomethyl-10-deacetylbaccatin III (709673-79-0) → 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene (183133-94-0)

Guidance literature:

With water; Raney nickel; In methanol; at 23 ℃;

upstream raw materials:

10-deacetylbaccatin III

dimethyl sulfate

methyl iodide

7,13-diacetyl baccatin III

Downstream raw materials:

1-hydroxy-7β,10β-di-methoxy-9-oxo-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-{(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-trethylsilyloxy-3-phenylpropanoate}

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-2-((((benzyloxy)carbonyl)glycyl)oxy)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoyl)oxy)-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

carbazitaxel

4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-11-taxene-13α-yl (2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Refernces

• 1、 Wang, Changwei,Chen, Lei,Sun, Yi,Guo, Wanrong,Taouil, Adam K.,Ojima, Iwao. "Design, synthesis and SAR study of Fluorine-containing 3rd-generation taxoids". . . Retrieved 2022/01/03.
• 2、 -. "Method for synthesizing cabazitaxel by using 10-deacetylbaccatin III". Paragraph 0017; 0021; 0025. . Retrieved 2018/06/23.