[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate

Base Information

• Chemical Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate
• CAS No.: 162459-94-1
• Molecular Formula: C52H75NO13Si2
• Molecular Weight: 978.337
• DSSTox Substance ID: DTXSID20472003
• Mol file: 162459-94-1.mol

Synonyms:162459-94-1;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate;FT-0675475;DTXSID20472003;7-O-(Triethylsilyl)-2 inverted exclamation mark -O-tert-butyl(dimethyl)silyl-2-debenzoyl Paclitaxel

Chemical Property of [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate

Chemical Property:

• Boiling Point: 905.1±65.0 °C(Predicted)
• PKA: 12.69±0.70(Predicted)
• PSA: 196.71000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 8.50480
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform, DIchloromethane, Ehtyl Acetate, Methanol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 19
• Exact Mass: 977.47769452
• Heavy Atom Count: 68
• Complexity: 1920

Purity/Quality:

≥95% ^*data from raw suppliers

7-O-(Triethylsilyl)-2’-O-tert-butyl(dimethyl)silyl-2-debenzoylPaclitaxel ^*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(C3O)(C4(C)C)O)OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O[Si](C)(C)C(C)(C)C)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]3O)(C4(C)C)O)OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O[Si](C)(C)C(C)(C)C)C)OC(=O)C)C)OC(=O)C
• Uses: Paclitaxel (P132500) derivative. Intermediate in the preparation of benzoyl-substituted paclitaxel analogs.

Technology Process of [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate

There total 10 articles about [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoate 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: 76.0%

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel (156413-61-5) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-7-(triethylsilyl)paclitaxel (162459-94-1)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane; -78 deg C, 5 min; -10 deg C;

DOI:10.1016/0040-4020(95)00823-Q

Reference yield: 15.0%

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel (156413-61-5) → 2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel (160768-75-2) + 2'-(tert-butyldimethylsilyl)-2-debenzoyl-7-(triethylsilyl)paclitaxel (162459-94-1)

Guidance literature:

With potassium hydroxide; potassium tert-butylate; In tetrahydrofuran; at -15 ℃; for 12h;

DOI:10.1021/jm960142x

Reference yield:

taxol (33069-62-4) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-7-(triethylsilyl)paclitaxel (162459-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) imidazole, 2.) imidazole / 1.) DMF, 60 deg C, 2 h, 2.) DMF, room temp., 1 h

2: Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

With 1H-imidazole; N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane;

DOI:10.1021/jo982095h

upstream raw materials:

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel

triethylsilyl chloride

taxol

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₅₂H₇₃NO₁₃Si₂

C₆₆H₈₅NO₁₅Si₂

C₅₇H₇₇NO₁₅Si₂

C₅₇H₇₇NO₁₄SSi₂