2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester
• CAS No.: 157430-91-6
• Molecular Formula: C₃₂H₆₀O₆SSi₂
• Molecular Weight: 629.062
• Mol file: 157430-91-6.mol

Synonyms:2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester

There total 15 articles about 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester 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: 100.0%

2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-7-phenylsulfanyl-3-triethylsilanyloxy-heptyl ester (179944-97-9) → 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester (157430-91-6)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 23 ℃; for 1.5h;

DOI:10.1021/jo9606113

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester (157430-91-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

4: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1 h / -23 °C

6: 74 percent / sodium bis(2-methoxyethoxy)aluminum hydride / 1,2-dimethoxy-ethane; toluene / 2 h / 0 °C

7: 99 percent / pyridine / 1.5 h / 0 °C

8: 99 percent / hydrogen / Pd on carbon / ethanol / 3.5 h / 23 °C

9: 91 percent / trubutylphosphine / dimethylformamide / 12 h / 23 °C

10: 100 percent / imidazole / dimethylformamide / 1.4 h / 23 °C

11: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.5 h / 23 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; (+)-Weinsaeure-diethylester; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-7-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-triethylsilanyloxy-heptyl ester (157430-91-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / pyridine / 1.5 h / 0 °C

2: 99 percent / hydrogen / Pd on carbon / ethanol / 3.5 h / 23 °C

3: 91 percent / trubutylphosphine / dimethylformamide / 12 h / 23 °C

4: 100 percent / imidazole / dimethylformamide / 1.4 h / 23 °C

5: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.5 h / 23 °C

With pyridine; 1H-imidazole; tributylphosphine; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9606113

upstream raw materials:

2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-7-phenylsulfanyl-3-triethylsilanyloxy-heptyl ester

triethylsilyl chloride

t-butyldimethylsiyl triflate

pivaloyl chloride

Downstream raw materials:

2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-10-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-4,6-dimethyl-3-triethylsilanyloxy-decyl ester

2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9,15-dimethoxy-4,6,10,13-tetramethyl-16-trityloxy-hexadec-10-enyl ester

2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

2,2-Dimethyl-propionic acid (Z)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-triethylsilanyloxy-16-trityloxy-hexadec-10-enyl ester

Refernces

• 1、 Kigoshi, Hideo,Ojika, Makoto,Ishigaki, Takeshi,Suenaga, Kiyotake,Mutou, Tsuyoshi,Sakakura, Akira,Ogawa, Takeshi,Yamada, Kiyoyuki. "Total synthesis of aplyronine A, a potent antitumor substance of marine origin". . p. 7443 - 7444. Retrieved 2007/10/02.