7,13-Bis-O-(triethylsilyl) Baccatin III

Base Information

• Chemical Name: 7,13-Bis-O-(triethylsilyl) Baccatin III
• CAS No.: 150541-99-4
• Molecular Formula: C43H66O11Si2
• Molecular Weight: 815.161
• DSSTox Substance ID: DTXSID50451543
• Nikkaji Number: J1.487.440B
• Wikidata: Q82271613
• Mol file: 150541-99-4.mol

Synonyms:150541-99-4;7,13-Bis(triethylsilyl)baccatin III;7,13-Bis-O-(triethylsilyl) Baccatin III;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,15-bis(triethylsilyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;DTXSID50451543;Benzoic acid 1-hydroxy-4,10beta-diacetoxy-7beta,13alpha-bis(triethylsiloxy)-9-oxo-5beta,20-epoxytaxa-11-ene-2alpha-yl ester

Chemical Property of 7,13-Bis-O-(triethylsilyl) Baccatin III

Chemical Property:

• PSA: 143.89000
• LogP: 7.71160
• Solubility.: Chloroform, Dichloromethane
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 17
• Exact Mass: 814.41436599
• Heavy Atom Count: 56
• Complexity: 1510

Purity/Quality:

98% ^*data from raw suppliers

7,13-Bis-O-(triethylsilyl)BaccatinIII ^*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[Si](CC)(CC)CC)C)OC(=O)C)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[Si](CC)(CC)CC)C)OC(=O)C)C)OC(=O)C
• Uses: Protected Baccatin III.

Technology Process of 7,13-Bis-O-(triethylsilyl) Baccatin III

There total 58 articles about 7,13-Bis-O-(triethylsilyl) 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) + baccatin III (27548-93-2) → 7,13-O,O-Bis(triethylsilyl)baccatin III (150541-99-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 23 - 50 ℃;

DOI:10.1021/ja8067534

Reference yield: 94.0%

phenyllithium (591-51-5) + 1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-2-debenzoylbaccatin III (175982-31-7) → 7,13-O,O-Bis(triethylsilyl)baccatin III (150541-99-4)

Guidance literature:

In tetrahydrofuran; diethyl ether; cyclohexane; at -78 ℃; for 0.25h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield: 63.0%

C41H64O10Si2 + acetyl chloride (75-36-5) → 7,13-O,O-Bis(triethylsilyl)baccatin III (150541-99-4)

Guidance literature:

C₄₁H₆₄O₁₀Si₂; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.333333h; Inert atmosphere;

acetyl chloride; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c03851

upstream raw materials:

triethylsilyl chloride

baccatin III

phenyllithium

1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-2-debenzoylbaccatin III

Downstream raw materials:

1-dimethylsilyl-7,13-bis(triethylsilane)baccatin III

C₄₃H₆₆O₁₀Si₂

C₆₄H₈₁NO₁₄Si₂

C₆₁H₈₁NO₁₄Si₂

Refernces

• 1、 Iiyama, Shota,Fukaya, Keisuke,Yamaguchi, Yu,Watanabe, Ami,Yamamoto, Hiroaki,Mochizuki, Shota,Saio, Ryosuke,Noguchi, Takashi,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka. "Total Synthesis of Paclitaxel". supporting information. p. 202 - 206. Retrieved 2021/12/27.
• 2、 Ondari, Mark E.,Walker, Kevin D.. "The taxol pathway 10-O-acetyltransferase shows regioselective promiscuity with the oxetane hydroxyl of 4-deacetyltaxanes". experimental part. p. 17187 - 17194. Retrieved 2009/04/13.