7-O-(Triethylsilyl) Paclitaxel

Base Information

• Chemical Name: 7-O-(Triethylsilyl) Paclitaxel
• CAS No.: 148930-55-6
• Molecular Formula: C₅₃H₆₅NO₁₄Si
• Molecular Weight: 968.183
• UNII: UV2YY7E35G
• DSSTox Substance ID: DTXSID00455637
• Wikidata: Q82277728
• Mol file: 148930-55-6.mol

Synonyms:148930-55-6;7-O-(Triethylsilyl)taxol;7-O-(Triethylsilyl) Paclitaxel;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;7-O-(Triethylsilyl)paclitaxel;7-(Triethylsilyl)taxol;UV2YY7E35G;7-O-(Triethylsilanyl)paclitaxel;DTXSID00455637;PACLITAXEL IMPURITY K [EP IMPURITY];4,10beta-bis(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-7beta-[(triethylsilyl)oxy]-5beta,20-epoxytax-11-en-2alpha-yl benzoate;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-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 7-O-(Triethylsilyl) Paclitaxel

Chemical Property:

• Melting Point: >150oC (dec.)
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 19
• Exact Mass: 967.41743228
• Heavy Atom Count: 69
• Complexity: 1960

Purity/Quality:

98% ^*data from raw suppliers

7-O-(Triethylsilyl)Paclitaxel ^*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(C3OC(=O)C5=CC=CC=C5)(C4(C)C)O)OC(=O)C(C(C6=CC=CC=C6)NC(=O)C7=CC=CC=C7)O)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]3OC(=O)C5=CC=CC=C5)(C4(C)C)O)OC(=O)[C@@H]([C@H](C6=CC=CC=C6)NC(=O)C7=CC=CC=C7)O)C)OC(=O)C)C)OC(=O)C
• Uses: Protected Paclitaxel. Paclitaxel - Impurity K. Protected Paclitaxel.

Technology Process of 7-O-(Triethylsilyl) Paclitaxel

There total 63 articles about 7-O-(Triethylsilyl) 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: 99.0%

2'-benzyloxycarbonyl-7-triethylsilyl taxol (148930-57-8) → 7-O-(triethylsilyl)paclitaxel (148930-55-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h;

DOI:10.1016/S0040-4020(01)80381-1

Reference yield: 76.0%

2'-O-benzyl-7-O-(triethylsilyl)paclitaxel (194420-28-5) → 7-O-(triethylsilyl)paclitaxel (148930-55-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; Ambient temperature;

DOI:10.1246/cl.1998.3

Reference yield:

(2'R,3S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol → 10-deacetylpaclitaxel (78432-77-6) + taxol (33069-62-4) + 7-O-(triethylsilyl)paclitaxel (148930-55-6) + 7-epipaclitaxel (105454-04-4)

Guidance literature:

With trifluoroacetic acid; In water; acetic acid; at 20 ℃; for 6h; Solvent; Reagent/catalyst; Concentration; Time;

DOI:10.1021/op020221k

upstream raw materials:

2'-benzyloxycarbonyl-7-triethylsilyl taxol

1-hydroxy-7β-triethylsilyloxy-9-oxo-10β-acetyloxy-5β,20-epoxytax-11-ene-2α,4,13α-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-benzoylamino-2-triethylsilyloxy-3-phenylpropanoate]

2'-O-benzyl-7-O-(triethylsilyl)paclitaxel

4-bromopent-4-en-1-ol

Downstream raw materials:

7-(triethylsilyl)baccatin III

C₅₅H₆₉NO₁₄SSi

taxol

2’-carboxybenzoylpaclitaxel

Refernces

• 1、 Dziedzic, Pawel,Schyman, Patrie,Kullberg, Martin,Cordova, Armando. "Highly enantioselective organocatalytic addition of aldehydes to N-(Phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues". supporting information; experimental part. p. 4044 - 4048. Retrieved 2009/12/01.
• 2、 Mukaiyama, Teruaki,Shiina, Isamu,Iwadare, Hayato,Saitoh, Masahiro,Nishimura, Toshihiro,Ohkawa, Naoto,Sakoh, Hiroki,Nishimura, Koji,Tani, Yu-Ichirou,Hasegawa, Masatoshi,Yamada, Koji,Saitoh, Katsuyuki. "Asymmetric total synthesis of Taxol". . p. 121 - 161. Retrieved 2007/10/03.