10-deacetyl-13-oxobaccatin III

Base Information

• Chemical Name: 10-deacetyl-13-oxobaccatin III
• CAS No.: 92950-42-0
• Molecular Formula: C29H34O10
• Molecular Weight: 542.57426
• ChEMBL ID: CHEMBL510651
• DSSTox Substance ID: DTXSID80570271
• Metabolomics Workbench ID: 140923
• Nikkaji Number: J626.880C
• Wikidata: Q82457655
• Mol file: 92950-42-0.mol

Synonyms:10-deacetyl-13-oxobaccatin III;92950-42-0;10-Deacetyl-13-Oxo-Baccatin III;[(1S,2S,3R,4S,7R,9S,10S,12R)-4-acetyloxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;13-Oxo-10-deacetyl Baccatin III;CHEMBL510651;DTXSID80570271;HY-W778562;CS-0855315;(5beta,7beta,10beta)-4-(Acetyloxy)-1,7,10-trihydroxy-9,13-dioxo-5,20-epoxytax-11-en-2-yl benzoate

Chemical Property of 10-deacetyl-13-oxobaccatin III

Chemical Property:

• Melting Point: 205-207 °C
• Boiling Point: 720.7±60.0 °C(Predicted)
• PKA: 11.06±0.70(Predicted)
• PSA: 156.66000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 1.29000
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 542.21519728
• Heavy Atom Count: 39
• Complexity: 1130

Purity/Quality:

99% ^*data from raw suppliers

13-Oxo-10-deacetylBaccatinIII ^*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)(CC1=O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O
• 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)(CC1=O)O)OC(=O)C5=CC=CC=C5)(CO4)OC(=O)C)O)C)O
• Uses: 13-Oxo-10-deacetyl Baccatin III is a novel stable derivative of 10-Deacetylbaccatin III (D198250) with antitumor and antimitotic activity.

Technology Process of 10-deacetyl-13-oxobaccatin III

There total 1 articles about 10-deacetyl-13-oxobaccatin 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: 39.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) → 13-dehydro-10-deacetylbaccatin III (92950-42-0) + 13-dehydro-5,O-seco-5-epi-5-acetyl-4,10-bisdeacetylbaccatin III

Guidance literature:

With N-Bromosuccinimide; In 1,4-dioxane; water; for 7h; Ambient temperature;

Reference yield: 91.0%

acetic anhydride (108-24-7) + 13-dehydro-10-deacetylbaccatin III (92950-42-0) → 7-O-acetyl-13-oxobaccatin III (32981-91-2) + 13-oxobaccatin III (32981-89-8)

Guidance literature:

With ytterbium trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 4h;

DOI:10.1021/jo0347112

Reference yield: 70.0%

triethylsilyl chloride (994-30-9) + 13-dehydro-10-deacetylbaccatin III (92950-42-0) → 7-triethylsilyl-13-dehydro-10-deacetylbaccatin III (155588-21-9)

Guidance literature:

With pyridine; for 22h; Ambient temperature;

DOI:10.1016/0040-4020(94)01078-E

upstream raw materials:

10-deacetylbaccatin III

Downstream raw materials:

7-triethylsilyl-13-dehydro-10-deacetylbaccatin III

7,10-di(triethylsilyl)-13-oxo-10-deacetylbaccatin III

7-O-acetyl-13-oxobaccatin III

13-oxobaccatin III

Refernces