7-O-(Triethylsilyl)-10-deacetyl Baccatin III

Base Information

• Chemical Name: 7-O-(Triethylsilyl)-10-deacetyl Baccatin III
• CAS No.: 115437-18-8
• Molecular Formula: C35H50 O10 Si
• Molecular Weight: 658.861
• Mol file: 115437-18-8.mol

Synonyms:7,11-Methano-5H-cyclodeca[3,4]benz[1,2-b]oxet-5-one,12b-(acetyloxy)-12-(benzoyloxy)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-dodecahydro-6,9,11-trihydroxy-4a,8,13,13-tetramethyl-4-[(triethylsilyl)oxy]-,[2aR-(2aa,4b,4ab,6b,9a,11a,12a,12aa,12ba)]-; 10-Deacetyl-7-triethylsilylbaccatin III;7-(Triethylsilyl)-10-deacetylbaccatin III; 7-O-(Triethylsilyl)-10-deacetylbaccatin III; 7-O-Triethylsilyl-10-desacetylbaccatin III

Chemical Property of 7-O-(Triethylsilyl)-10-deacetyl Baccatin III

Chemical Property:

• Refractive Index: 1.572
• PSA: 148.82000
• LogP: 4.11130
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

98.5% ^*data from raw suppliers

7-O-(Triethylsilyl)-10-deacetylBaccatinIII ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-O-(Triethylsilyl)-10-deacetyl Baccatin III (cas# 115437-18-8_x000D_) is a compound useful in organic synthesis.

Technology Process of 7-O-(Triethylsilyl)-10-deacetyl Baccatin III

There total 6 articles about 7-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: 100.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + triethylsilyl chloride (994-30-9) → 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

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

Reference yield: 91.0%

10-deacetylbaccatin III (32981-86-5,172018-16-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8)

Guidance literature:

With pyridine; at 25 ℃; for 17h;

DOI:10.1021/ja00107a006

Reference yield: 81.0%

13-Acetyl-7-(triethylsilyl)baccatin III (152448-78-7) → 7-triethylsilyl-10-deacetylbaccatin III (115437-18-8)

Guidance literature:

With hydrazine hydrate; In ethanol; for 8h; Ambient temperature;

DOI:10.1021/jo00108a053

upstream raw materials:

10-deacetylbaccatin III

triethylsilyl chloride

tert-butyldimethylsilyl chloride

13-Acetyl-7-(triethylsilyl)baccatin III

Downstream raw materials:

10-deacetyl-10-(S-methylxanthyl)-7-(triethylsilyl)baccatin III

C₃₉H₅₅NO₁₁Si

C₄₀H₅₈O₁₁Si

C₄₀H₅₉NO₁₁Si

Refernces

• 1、 Shiina, Isamu,Saitoh, Masahiro,Nishimura, Koji,Saitoh, Katsuyuki,Mukaiyama, Teruaki. "New and effective synthesis of 7-triethylsilylbaccatin III from 7β,13α-bistriethylsiloxy-1β,2α,10β-trihydroxy-9-oxo- 4(20),11-taxadiene". . p. 223 - 224. Retrieved 1996.
• 2、 Dong, Yi,Wang, Suhua,Wang, Chunting,Li, Zihua,Ma, Yao,Liu, Gang. "Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis". . p. 1219 - 1224. Retrieved 2017.
• 3、 Nicolaou,Nantermet,Ueno,Guy,Couladouros,Sorensen. "Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution". . p. 624 - 633. Retrieved 1995.
• 4、 -. "Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound". Paragraph 0048; 0085-0089. . Retrieved 2019/08/30.