7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin III

Base Information

• Chemical Name: 7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin III
• CAS No.: 149107-84-6
• Molecular Formula: C41H64 O10 Si2
• Molecular Weight: 773.124
• DSSTox Substance ID: DTXSID60471292
• Nikkaji Number: J1.317.899B
• Wikidata: Q82299774
• Mol file: 149107-84-6.mol

Synonyms:7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin III;149107-84-6;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;SCHEMBL13531083;DTXSID60471292;AKOS025294554;J-008553;(5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,13-dihydroxy-9-oxo-7,10-bis[(triethylsilyl)oxy]-5,20-epoxytax-11-en-2-yl benzoate

Chemical Property of 7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin III

Chemical Property:

• Refractive Index: 1.542
• PSA: 137.82000
• LogP: 7.14080
• Solubility.: Chloroform, Ethyl Acetate
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 15
• Exact Mass: 772.40380130
• Heavy Atom Count: 53
• Complexity: 1400

Purity/Quality:

98%Min ^*data from raw suppliers

7,10-Bis[O-(triethylsilyl)]-10-deacetylBaccatinIII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[Si](CC)(CC)OC1CC2C(CO2)(C3C1(C(=O)C(C4=C(C(CC(C3OC(=O)C5=CC=CC=C5)(C4(C)C)O)O)C)O[Si](CC)(CC)CC)C)OC(=O)C
• Isomeric SMILES: CC[Si](CC)(CC)O[C@H]1C[C@@H]2[C@@](CO2)([C@@H]3[C@@]1(C(=O)[C@@H](C4=C([C@H](C[C@@]([C@H]3OC(=O)C5=CC=CC=C5)(C4(C)C)O)O)C)O[Si](CC)(CC)CC)C)OC(=O)C
• Uses: Intermediate for the preparation of Docetaxel

Technology Process of 7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin III

There total 6 articles about 7,10-Bis[O-(triethylsilyl)]-10-deacetyl Baccatin 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: 95.0%

triethylsilyl chloride (994-30-9) + 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8) → 7,10-bis(triethylsilyl)-10-deacetylbaccatin III (149107-84-6)

Guidance literature:

7-triethylsilyl-10-deacetylbaccatin III; With n-butyllithium; In tetrahydrofuran;

triethylsilyl chloride; In tetrahydrofuran; at 0 ℃;

Reference yield: 89.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + triethylsilyl chloride (994-30-9) → 7,10-bis(triethylsilyl)-10-deacetylbaccatin III (149107-84-6)

Guidance literature:

10-deacetylbaccatin III; triethylsilyl chloride; With dmap; triethylamine; In tetrahydrofuran; at 25 ℃; Inert atmosphere;

With lithium bromide; In tetrahydrofuran; at 20 - 70 ℃; Inert atmosphere;

Reference yield: 49.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + triethylsilyl chloride (994-30-9) → 7,10-bis(triethylsilyl)-10-deacetylbaccatin III (149107-84-6) + 7,10,13-tris(triethylsilyl)-10-deacetylbaccatin III (194720-19-9) + 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,10β-dihydroxy-9-oxo-7β,13α-di(triethylsilyloxy)-11-taxene (183133-99-5) + 7,10,13,1'-tetraTES 2-debenzoyl-10-deacetylbaccatin III-1,2-semiorthobenzoate

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 96h; Further byproducts given; Ambient temperature;

DOI:10.1016/S0040-4020(99)00290-2

upstream raw materials:

10-deacetylbaccatin III

triethylsilyl chloride

7-triethylsilyl-10-deacetylbaccatin III

Downstream raw materials:

Docetaxel

Refernces

• 1、 Ma, Yun-Tao,Yang, Yanting,Cai, Pei,Sun, De-Yang,Sánchez-Murcia, Pedro A.,Zhang, Xiao-Ying,Jia, Wen-Qiang,Lei, Lei,Guo, Mengqi,Gago, Federico,Wang, Hongbo,Fang, Wei-Shuo. "A Series of Enthalpically Optimized Docetaxel Analogues Exhibiting Enhanced Antitumor Activity and Water Solubility". supporting information. p. 524 - 533. Retrieved 2018/03/30.
• 2、 -. "Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups". Page 39. . Retrieved 2010/02/06.