2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel

Base Information

• Chemical Name: 2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel
• CAS No.: 160768-75-2
• Molecular Formula: C₅₀H₇₃NO₁₂Si₂
• Molecular Weight: 936.3
• UNII: Q9W4QT7E7A
• Mol file: 160768-75-2.mol

Synonyms:160768-75-2;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-Acetyloxy-1,2,4-trihydroxy-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;2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel;Q9W4QT7E7A;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6-(Acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11,12,12b-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[(triethylsilyl)oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (alphaR,betaS)-beta-(benzoylamino)-alpha-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzenepropanoate;Benzenepropanoic acid, beta-(benzoylamino)-alpha-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6-(acetyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11,12,12b-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[(triethylsilyl)oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-

Chemical Property of 2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel

Chemical Property:

• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 17
• Exact Mass: 935.46712983
• Heavy Atom Count: 65
• Complexity: 1810

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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)O
• 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)O

Technology Process of 2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel

There total 12 articles about 2'-O-tert-Butyl(dimethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel 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: 75.0%

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)

Guidance literature:

With potassium tert-butylate; water; In tetrahydrofuran; at -20 ℃; for 72h;

DOI:10.1016/0040-4039(94)88392-0

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'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel (160768-75-2)

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: 66 percent / 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

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-4-methoxycarbonyl-7-(triethylsilyl)paclitaxel 1,2-carbonate

2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-1,2-carbonato-paclitaxel

triethylsilyl chloride

Downstream raw materials:

2'-O-(tert-butyldimethylsilyl)-7-O-triethylsilyl-2-debenzoyl-4-deacetyl-1,2-carbonato-paclitaxel

2'-tert-butyldimethylsilyl-4-deacetyl-7-(triethylsilyl)paclitaxel

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel 1,2-carbonate