(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

Base Information

• Chemical Name: (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran
• CAS No.: 860267-68-1
• Molecular Formula: C₃₀H₅₂O₇S
• Molecular Weight: 556.805
• Mol file: 860267-68-1.mol

Synonyms:(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

Chemical Property of (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

There total 14 articles about (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran 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: 90.0%

(1R,2'R,5'R,6'R)-1-(5'-methoxymethoxy-6'-tetradecyl-tetrahydropyran-2'-yl)-ethane-1,2-diol (860267-67-0) + p-toluenesulfonyl chloride (98-59-9) → (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran (860267-68-1)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/ol0508126

Reference yield:

(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol (860267-60-3) → (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran (860267-68-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

2.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

3.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

4.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

5.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

6.1: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

7.1: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

8.1: 2.53 g / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

9.2: 3.28 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

10.1: 939 mg / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 12 h / 50 °C

11.1: 616 mg / hydrogen / Pd/C / ethanol / 46 h / 20 °C

12.1: 90 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 18 h / 20 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; n-butyllithium; samarium diiodide; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: oxy-Michael addition / 7.1: Mitsunobu reaction / 9.2: Wittig reaction;

DOI:10.1021/ol0508126

Reference yield:

3-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde → (1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran (860267-68-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

2.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

3.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

4.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

5.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

6.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

7.1: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

8.1: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

9.1: 2.53 g / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

10.2: 3.28 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

11.1: 939 mg / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 12 h / 50 °C

12.1: 616 mg / hydrogen / Pd/C / ethanol / 46 h / 20 °C

13.1: 90 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 18 h / 20 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; n-butyllithium; samarium diiodide; (1S)-10-camphorsulfonic acid; hydrogen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: oxy-Michael addition / 8.1: Mitsunobu reaction / 10.2: Wittig reaction;

DOI:10.1021/ol0508126

upstream raw materials:

(1R,2'R,5'R,6'R)-1-(5'-methoxymethoxy-6'-tetradecyl-tetrahydropyran-2'-yl)-ethane-1,2-diol

p-toluenesulfonyl chloride

(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane