2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate

Base Information

• Chemical Name: 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate
• CAS No.: 186348-04-9
• Molecular Formula: C₆₂H₉₃NO₁₆Si₂
• Molecular Weight: 1164.59
• Mol file: 186348-04-9.mol

Synonyms:2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate

Chemical Property of 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate

There total 10 articles about 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate 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:

triethylsilyl chloride (994-30-9) → 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate (186348-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine / dimethylformamide / 4 h / Ambient temperature

2: 80 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

3: 1.) LiHMDS / 1.) THF, hexane, -40 deg C, 10 min, 2.) THF, hexane, from -40 deg C to RT, 30 min

4: 1.) LiHMDS / 1.) THF, -45 deg C, 2 min, 2.) THF, -45 deg C, 10 min

With pyridine; lithium hexamethyldisilazane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm960563e

Reference yield:

3,3-dimethyl acrylaldehyde (107-86-8) → 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate (186348-04-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / Na₂SO₄ / CH₂Cl₂ / 1 h

2: 1.) LDA / 1.) THF, hexane, -84 deg C, 2 h, 2.) THF, hexane, a) -84 deg C, 2 h, b) from -84 deg C to RT, overnight

3: 90 percent / aq. ammonium cerium(IV) nitrate / acetonitrile / -5 °C

4: 89 percent / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) LiHMDS / 1.) THF, -45 deg C, 2 min, 2.) THF, -45 deg C, 10 min

With dmap; ammonium cerium(IV) nitrate; sodium sulfate; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; In dichloromethane; acetonitrile;

DOI:10.1021/jm960563e

Reference yield:

Hexanoyl chloride (142-61-0) → 2'-[(triisopropylsilyl)oxy]-3'-dephenyl-3'-(2-methyl-1-propenyl)-3'-N-hexanoyl-7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxydocetaxel 1,14-carbonate (186348-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) LiHMDS / 1.) THF, -45 deg C, 2 min, 2.) THF, -45 deg C, 10 min

With dmap; triethylamine; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jm960563e

upstream raw materials:

(3R,4S)-1-Hexanoyl-4-(2-methyl-propenyl)-3-triisopropylsilanyloxy-azetidin-2-one

7-(triethylsilyl)-10-((E)-2-butenoyl)-14β-hydroxy-10-deacetylbaccatin III 1,14-carbonate

triethylsilyl chloride

3,3-dimethyl acrylaldehyde