(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
Hs Code.:

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

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

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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%

: 860267-67-0
(1R,2'R,5'R,6'R)-1-(5'-methoxymethoxy-6'-tetradecyl-tetrahydropyran-2'-yl)-ethane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 860267-68-1
(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/ol0508126

Reference yield:

: 860267-60-3
(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

: 860267-68-1
(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

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

: 860267-68-1
(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran

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