2'-epi-Taxotere

Base Information

• Chemical Name: 2'-epi-Taxotere
• CAS No.: 133577-33-0
• Molecular Formula: C₄₃H₅₃NO₁₄
• Molecular Weight: 807.892
• DSSTox Substance ID: DTXSID80928192
• Wikidata: Q82902942
• Mol file: 133577-33-0.mol

Synonyms:133577-33-0;2'-Epi Docetaxel;S-Erythro-taxotere;2'-epi-Taxotere;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2S,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;2-Epi Docetaxel Impurity;SCHEMBL16811735;DTXSID80928192;ZDZOTLJHXYCWBA-KWUUUEAUSA-N;(alphaS,betaS)-beta-[[(1,1-Dimethylethoxy)carbonyl]amino]-alpha-hydroxybenzenepropanoic 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-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H;4-(Acetyloxy)-13-[(3-{[tert-butoxy(hydroxy)methylidene]amino}-2-hydroxy-3-phenylpropanoyl)oxy]-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate

Chemical Property of 2'-epi-Taxotere

Chemical Property:

• Melting Point: 180-183°C (dec.)
• Boiling Point: 900.5±65.0 °C(Predicted)
• PKA: 11.20±0.46(Predicted)
• PSA: 218.71000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 3.73750
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 13
• Exact Mass: 807.34660536
• Heavy Atom Count: 58
• Complexity: 1660

Purity/Quality:

99% ^*data from raw suppliers

2’-EpiDocetaxel ^*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)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(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)(C[C@@H]1OC(=O)[C@H]([C@H](C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
• Uses: An impurity of Docetaxel (D494420).

Technology Process of 2'-epi-Taxotere

There total 133 articles about 2'-epi-Taxotere 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%

di-tert-butyl dicarbonate (24424-99-5) + (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate (133524-69-3,133577-36-3,133577-37-4) → Docetaxel (114915-20-7,114977-28-5,114977-29-6,133577-32-9,133577-33-0)

Guidance literature:

Reference yield: 92.8%

2'-acetyldocetaxel (151509-27-2) → Docetaxel (114915-20-7,114977-28-5,114977-29-6,133577-32-9,133577-33-0)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/cjoc.201201142

Reference yield: 90.0%

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel (114915-14-9) → Docetaxel (114915-20-7,114977-28-5,114977-29-6,133577-32-9,133577-33-0)

Guidance literature:

With acetic acid; zinc; In methanol; at 60 ℃; for 2h;

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

upstream raw materials:

di-tert-butyl dicarbonate

C₃₈H₄₅NO₁₂

7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III

(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate

Downstream raw materials:

C₄₃H₅₃NO₁₄

docetaxel 2'-succinic ester

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

N-tert-butoxycarbonyl-10-deacetyl-N-debenzoyl-taxol trihydrate

Refernces

• 1、 Xue, Baoyu,Zhao, Junhong,Fan, Yange,Chen, Shipeng,Li, Wenfeng,Chen, Jin,Li, Zheng,Wang, Hongxing,Kong, Hongjun. "Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes". . . Retrieved 2020/02/05.
• 2、 -. "Method for synthesizing cabazitaxel from 10-deacetylbaccatin III". . . Retrieved 2019/09/17.