(10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane

Base Information

• Chemical Name: (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane
• CAS No.: 230966-23-1
• Molecular Formula: C₃₉H₇₀O₄S
• Molecular Weight: 635.048
• Mol file: 230966-23-1.mol

Synonyms:(10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane

Chemical Property of (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane

There total 9 articles about (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane 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: 78.0%

9-(tetrahydropyran-2-yl)oxynonyl iodide (141780-02-1) + (R)-4-methyl-1-phenylsulfonyloctadecane (230966-21-9) → (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane (230966-23-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; for 10h; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<981::AID-EJOC981>3.0.CO;2-3

Reference yield:

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane (230966-23-1)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine

2: 35.8 g / Li₂CuCl₄ / tetrahydrofuran / 12 h / -78 °C / to RT

3: 1.) O₃, NaHCO₃; 2.) NaBH₄ / 1.) n-hexane, MeOH, CH₂Cl₂, -78 deg C, 10 h; 2.) n-hexane, MeOH, CH₂Cl₂, -78 deg C to 0 deg C, 3 h

4: 98 percent / pyridine / 12 h / 4 °C

5: 98 percent / NaI, NaHCO₃ / acetone / 4 h / Heating

6: 94 percent / dimethylformamide / 10 h / Ambient temperature

7: 78 percent / n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 10 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; dilithium tetrachlorocuprate; sodium hydrogencarbonate; ozone; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<981::AID-EJOC981>3.0.CO;2-3

Reference yield:

1,9-Nonanediol (3937-56-2) → (10RS,13R)-13-methyl-10-phenylsulfonyl-1-(tetrahydropyran-2-yl)oxyheptacosane (230966-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / p-TsOH*H₂O / CH₂Cl₂ / 2 h / Ambient temperature

2: pyridine / 12 h / 4 °C

3: NaI, NaHCO₃ / acetone / 4 h / Heating

4: 78 percent / n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 10 h / Ambient temperature

With n-butyllithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<981::AID-EJOC981>3.0.CO;2-3

upstream raw materials:

9-(tetrahydropyran-2-yl)oxynonyl iodide

(R)-4-methyl-1-phenylsulfonyloctadecane

(S)-3,7-dimethyl-6-octen-1-ol

1,9-Nonanediol

Refernces