2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-paclitaxel

Base Information

• Chemical Name: 2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-paclitaxel
• CAS No.: 165065-08-7
• Molecular Formula: C53H65 N O15 Si
• Molecular Weight: 984.182
• Nikkaji Number: J985.083J
• Mol file: 165065-08-7.mol

Synonyms:2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-paclitaxel;165065-08-7;2'-O-(tert-Butyldimethylsilyl)-6alpha-hydroxy-7-epi-paclitaxel;J-010181;2'-O-(tert-Butyldimethylsilyl)-6 alpha -hydroxy-7-epi-paclitaxel;(alphaR,betaS)-alpha-(tert-Butyldimethylsiloxy)-beta-(benzoylamino)benzenepropionic acid 1,6alpha,7alpha-trihydroxy-2alpha-(benzoyloxy)-4,10beta-diacetoxy-9-oxo-5beta,20-epoxytaxa-11-ene-13alpha-yl ester

Chemical Property of 2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-paclitaxel

Chemical Property:

• PSA: 230.52000
• LogP: 6.12690
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 17
• Exact Mass: 983.41234690
• Heavy Atom Count: 70
• Complexity: 2050

Purity/Quality:

98%Min ^*data from raw suppliers

2''-O-(tert-Butyldimethylsilyl)-6α-hydroxy7-epi-Paclitaxel ^*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(C(C(C2(C)C)(CC1OC(=O)C(C(C4=CC=CC=C4)NC(=O)C5=CC=CC=C5)O[Si](C)(C)C(C)(C)C)O)OC(=O)C6=CC=CC=C6)C7(COC7C(C3O)O)OC(=O)C)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@]3([C@H]([C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C4=CC=CC=C4)NC(=O)C5=CC=CC=C5)O[Si](C)(C)C(C)(C)C)O)OC(=O)C6=CC=CC=C6)[C@@]7(CO[C@@H]7[C@H]([C@H]3O)O)OC(=O)C)C)OC(=O)C
• Uses: 6a-Hydroxypaclitaxel derivative 6α-Hydroxypaclitaxel derivative.

Technology Process of 2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-paclitaxel

There total 5 articles about 2'-O-(tert-Butyldimethylsilyl)-6a-hydroxy-7-epi-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: 85.0%

2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel (165065-02-1) → 2'-O-(tert-butyldimethylsilyl)-6α-hydroxy-7-epipaclitaxel (165065-08-7)

Guidance literature:

With osmium(VIII) oxide; In tetrahydrofuran; pyridine; at 25 ℃;

DOI:10.1016/S0960-894X(97)00337-5

Reference yield:

2'-O-(tert-butyldimethylsilyl)paclitaxel (114655-02-6) → 2'-O-(tert-butyldimethylsilyl)-6α-hydroxy-7-epipaclitaxel (165065-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Tf₂O, 2.) DBU / 1.) pyridine, 25 deg C, 2.) 25 deg C

2: 85 percent / OsO₄ / pyridine; tetrahydrofuran / 25 °C

With osmium(VIII) oxide; trifluoromethylsulfonic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; pyridine;

DOI:10.1016/S0960-894X(97)00337-5

Reference yield:

taxol (33069-62-4) → 2'-O-(tert-butyldimethylsilyl)-6α-hydroxy-7-epipaclitaxel (165065-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / imidazole / dimethylformamide

2: 1.) Tf₂O, 2.) DBU / 1.) pyridine, 25 deg C, 2.) 25 deg C

3: 85 percent / OsO₄ / pyridine; tetrahydrofuran / 25 °C

With 1H-imidazole; osmium(VIII) oxide; trifluoromethylsulfonic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)00337-5

upstream raw materials:

2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel

taxol

tert-butyldimethylsilyl chloride

2'-O-(tert-butyldimethylsilyl)paclitaxel

Downstream raw materials:

C₆₀H₇₁NO₁₇SSi

2'-TBDMS-C-norpaclitaxel

2'-O-(t-butyldimethylsilyl)-C-seco-paclitaxel

2'-O-(tert-butyldimethylsilyl)-6α-trifluoromethanesulfuryl-7-epipaclitaxel

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