N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL

Base Information

• Chemical Name: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL
• CAS No.: 114915-16-1
• Molecular Formula: C44H47Cl6NO16
• Molecular Weight: 1058.57
• Mol file: 114915-16-1.mol

Synonyms:N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL;(αR,βS)-β-AMino-α-hydroxy-benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S, 12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy

Chemical Property of N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL

Chemical Property:

• PSA: 242.74000
• LogP: 7.30970
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl}Docetaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A intermediate in the synthesis of a metabolite of Docetaxel, an antineoplastic. An intermediate in partial synthesis of major human metabolites of Docetaxel (D494420), an antineoplastic.

Technology Process of N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL

There total 13 articles about N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL 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: 78.0%

4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate (143527-76-8) → 10-deacetyl-7,10-diTroc-baccatin III (114915-16-1)

Guidance literature:

With formic acid; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(00)79128-3

Reference yield: 75.0%

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel (114915-14-9) → 10-deacetyl-7,10-diTroc-baccatin III (114915-16-1)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)81313-2

Reference yield: 75.0%

C49H55Cl6NO18 (114977-25-2) → C44H47Cl6NO16 (114915-16-1,125354-11-2)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)81313-2

upstream raw materials:

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate

(2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester

Downstream raw materials:

N-de-tert-butoxycarbonyl-N-[2-(1-fluoro-2-methyl)-propyloxycarbonyl]-7,10-di(2,2,2-trichloroethyloxycarbonyl)-docetaxel

N-de-tert-butoxycarbonyl-N-[2-(1,1-difluoro-2-methyl)-propyloxycarbonyl]-7,10-di(2,2,2-trichloroethyloxycarbonyl)-docetaxel

N-de-tert-butoxycarbonyl-N-[2-(1,1,1-trifluoro-2-methyl)-propyloxycarbonyl]-7,10-di(2,2,2-trichloroethyloxycarbonyl)-docetaxel

Refernces

• 1、 -. "Method for preparing taxane natural product". Paragraph 0039-0041; 0048-0049; 0053-0054. . Retrieved 2019/11/20.
• 2、 -. "PREPARATION OF DOCETAXEL". Page/Page column 24. . Retrieved 2010/07/10.