13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III

Base Information

• Chemical Name: 13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III
• CAS No.: 143527-76-8
• Molecular Formula: C52H59Cl6NO18
• Molecular Weight: 1198.75
• Mol file: 143527-76-8.mol

Synonyms:143527-76-8;5-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-Acetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(2,2,2-trichloroethoxycarbonyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] 3-O-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate;13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III;LLLJXWNWAFHRTB-CHFAFVNJSA-N

Chemical Property of 13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III

Chemical Property:

• PSA: 235.26000
• LogP: 9.74610
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 9.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 19
• Exact Mass: 1197.183380
• Heavy Atom Count: 77
• Complexity: 2340

Purity/Quality:

13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl}BaccatinIII ^*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)C5C(N(C(O5)(C)C)C(=O)OC(C)(C)C)C6=CC=CC=C6)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)OCC(Cl)(Cl)Cl
• 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]5[C@@H](N(C(O5)(C)C)C(=O)OC(C)(C)C)C6=CC=CC=C6)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)OC(=O)OCC(Cl)(Cl)Cl)C)OC(=O)OCC(Cl)(Cl)Cl
• Uses: An intermediate in the synthesis of a metabolite of Docetaxel, an antineoplastic.

Technology Process of 13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III

There total 11 articles about 13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} 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: 99.0%

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III (95603-44-4) + (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid (143615-03-6,143527-70-2) → 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)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In toluene;

DOI:10.1007/s10600-012-0357-3

Reference yield:

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

2: 76 percent / NaHCO₃ / CH₂Cl₂ / 20 °C

3: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C

4: 100 percent / LiOH, H₂O / ethanol / 20 °C

5: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C

With dmap; lithium hydroxide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate; toluene;

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

Reference yield:

benzaldehyde (100-52-7) → 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)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Et₃N, Bu₂BOTf / 1.) CH₂Cl₂, -70 to 20 deg C, 2 h, 2.) -78 to 0 deg C, 1 h

2: 81 percent / tetrahydrofuran / 0.25 h / -75 - 15 °C

3: 99 percent / NaN₃, NH₄Cl / ethanol / 8 h / 60 °C

4: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

5: 76 percent / NaHCO₃ / CH₂Cl₂ / 20 °C

6: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C

7: 100 percent / LiOH, H₂O / ethanol / 20 °C

8: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C

With dmap; lithium hydroxide; sodium azide; di-n-butylboryl trifluoromethanesulfonate; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ammonium chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; toluene;

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

upstream raw materials:

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

di-tert-butyl dicarbonate

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

Downstream raw materials:

10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]