(2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol
• CAS No.: 157220-43-4
• Molecular Formula: C₂₈H₄₄O₃SSi
• Molecular Weight: 488.807
• Mol file: 157220-43-4.mol

Synonyms:(2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol

Chemical Property of (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol

There total 10 articles about (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol 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%

diphenyldisulfane (882-33-7) + (2S,3S,4S,5S)-7-Benzyloxy-2,4-dimethyl-5-triethylsilanyloxy-heptane-1,3-diol (157220-42-3) → (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol (157220-43-4)

Guidance literature:

With tributylphosphine; In N,N-dimethyl-formamide; at 23 ℃; for 4h;

DOI:10.1021/jo9606113

Reference yield:

triethylsilyl chloride (994-30-9) → (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol (157220-43-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / imidazole / dimethylformamide / 0.58 h / 23 °C

2: 98 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 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 / 1.5 h / -78 °C

5: 99 percent / molecular sieves 4A, titanium tetraisopropoxide, (-)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 2 h / -23 °C

6: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 0 deg C

7: 99 percent / trubutylphosphine / dimethylformamide / 4 h / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; diisobutylaluminium hydride; (-)-diethyl tartrate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (2R,3R,4S,5S)-7-Benzyloxy-2,4-dimethyl-1-phenylsulfanyl-5-triethylsilanyloxy-heptan-3-ol (157220-43-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 1.) trimethylaluminum / 1.) THF, toluene, 0 deg C -> room temperature, 2.) THF, toluene, CH₂Cl₂, -10 -> 0 deg C

3: 100 percent / imidazole / dimethylformamide / 0.58 h / 23 °C

4: 98 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

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

6: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 °C

7: 99 percent / molecular sieves 4A, titanium tetraisopropoxide, (-)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 2 h / -23 °C

8: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 0 deg C

9: 99 percent / trubutylphosphine / dimethylformamide / 4 h / 23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tributylphosphine; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; trimethylaluminum; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

upstream raw materials:

diphenyldisulfane

(2S,3S,4S,5S)-7-Benzyloxy-2,4-dimethyl-5-triethylsilanyloxy-heptane-1,3-diol

triethylsilyl chloride

3-Benzyloxypropanal

Downstream raw materials:

C₃₄H₅₈O₃SSi₂

C₃₄H₅₈O₅SSi₂

(2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

Refernces

• 1、 Kigoshi, Hideo,Ojika, Makoto,Suenaga, Kiyotake,Mutou, Tsuyoshi,Hirano, Junko,Sakakura, Akira,Ogawa, Takeshi,Nisiwaki, Masanori,Yamada, Kiyoyuki. "Synthetic studies on aplyronine A, a potent antitumor substance of marine origin: Stereocontrolled synthesis of the C21-C34 segment". . p. 1247 - 1250. Retrieved 2007/10/02.