<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

Base Information

Chemical Name:<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran
CAS No.:113453-62-6
Molecular Formula:C₁₈H₂₆O₃
Molecular Weight:290.403
Hs Code.:

Synonyms:<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

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Chemical Property of <6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

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Technology Process of <6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

There total 9 articles about <6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)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: 93.0%

: 113453-60-4
<2S,3R,6R,6(2S)>-2-ethyl-6-(1,2-dihydroxy-1-methylethyl)-3-methyl-3-(phenylmethoxy)tetrahydropyran

: 113453-62-6
<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

Guidance literature:: With p-toluenesulfonyl chloride; In pyridine; for 14h; Ambient temperature;
DOI:10.1021/ja00216a026

Reference yield:

: 96481-55-9,2088-07-5
2-methylpent-1-en-3-ol

: 113453-62-6
<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

Guidance literature:: Multi-step reaction with 9 steps

1: 1) (+)-diisopropyl tartrate, Ti(O-i-Pr)4; 2) TBHP / 1) CH₂Cl₂, -20 deg C, 15 min; 2) benzene, -20 deg C, 33 h

2: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 °C

3: 100 percent / tetrahydrofuran / 16 h / Ambient temperature

4: 95 percent / KH / tetrahydrofuran / 25 °C

6: 91 percent / DDQ / CH₂Cl₂; H₂O

7: 91 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

8: 1) Ti(O-i-Pr)4, (+)-diethyl tartrate, 2) TBHP, FeSO₄ / 1) CH₂Cl₂, -20 deg C, 15 min, 2) -30 deg C, 1 h, -20 deg C, 10 h

9: 93 percent / tosyl chloride / pyridine / 14 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; potassium hydride; sodium hydride; diisobutylaluminium hydride; iron(II) sulfate; (+)-Weinsaeure-diethylester; p-toluenesulfonyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00216a026

Reference yield:

: 84599-41-7
(R^*,S^*)-α-Ethyl-2-methyloxiranemethanol

: 113453-62-6
<6R,6(1S),3R,2S>-2-ethyl-3-methyl-6-(2-methyloxiran-2-yl)-3-(phenylmethoxy)tetrahydropyran

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 4 h / 0 °C

2: 100 percent / tetrahydrofuran / 16 h / Ambient temperature

3: 95 percent / KH / tetrahydrofuran / 25 °C

5: 91 percent / DDQ / CH₂Cl₂; H₂O

6: 91 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

7: 1) Ti(O-i-Pr)4, (+)-diethyl tartrate, 2) TBHP, FeSO₄ / 1) CH₂Cl₂, -20 deg C, 15 min, 2) -30 deg C, 1 h, -20 deg C, 10 h

8: 93 percent / tosyl chloride / pyridine / 14 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydride; sodium hydride; diisobutylaluminium hydride; iron(II) sulfate; (+)-Weinsaeure-diethylester; p-toluenesulfonyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00216a026