(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

Base Information

Chemical Name:(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol
CAS No.:209474-18-0
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

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Chemical Property of (R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

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Technology Process of (R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

There total 20 articles about (R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-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: 78.0%

: 337971-11-6
(2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran

: 209474-18-0
(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

Guidance literature:: With aluminum isopropoxide; In toluene; for 36h; Heating;
DOI:10.1016/S0040-4020(00)01129-7

Reference yield:

: 209474-16-8
(R)-(Z)-2-[5-(2-hydroxyethylidene)tetrahydropyran-2-yl]propan-2-ol

: 209474-18-0
(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / triethylamine / CH₂Cl₂ / 12 h / 20 °C

2: 41 percent / 4-dimethylaminopyridine; triethylamine; MsCl / CH₂Cl₂ / 2 h / 20 °C

3: 91 percent / mCPBA / CH₂Cl₂ / 72 h / -10 °C

4: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C

5: 99 percent / NaH / dimethylformamide / 7 h / 20 °C

6: 78 percent / aluminum triisopropoxide / toluene / 36 h / Heating

With dmap; sodium hydroxide; aluminum isopropoxide; sodium hydride; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(00)01129-7

Reference yield:

: 209474-15-7
(R)-(Z)-2-[2-(2,2,5,5-tetramethyl[1,3]dioxolan-4-yl)ethyl]but-2-ene-1,4-diol

: 209474-18-0
(R)-(5'Z)-2-{5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl}prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 98 percent / pyridine / 2 h / 20 °C

2: 91 percent / p-TsOH; H₂O / methanol / 44 h / 20 - 50 °C

3: 1.179 g / pyridine / 15 h / 20 °C

4: K₂CO₃ / methanol / 1.5 h / 20 °C

5: 0.432 g / aq. NaOH / methanol / 20 h / 20 °C

6: 95 percent / triethylamine / CH₂Cl₂ / 12 h / 20 °C

7: 41 percent / 4-dimethylaminopyridine; triethylamine; MsCl / CH₂Cl₂ / 2 h / 20 °C

8: 91 percent / mCPBA / CH₂Cl₂ / 72 h / -10 °C

9: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C

10: 99 percent / NaH / dimethylformamide / 7 h / 20 °C

11: 78 percent / aluminum triisopropoxide / toluene / 36 h / Heating

With pyridine; dmap; sodium hydroxide; water; aluminum isopropoxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(00)01129-7