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

Base Information

• Chemical Name: (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran
• CAS No.: 337971-11-6
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 337971-11-6.mol

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

Chemical Property of (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran

There total 18 articles about (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)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: 99.0%

p-methoxybenzyl chloride (824-94-2) + (6'R,1''RS)-(2Z)-2-[6'-(1''-methyloxiranyl)tetrahydropyran-3'-ylidene]ethanol (337971-09-2) → (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran (337971-11-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 7h;

DOI:10.1016/S0040-4020(00)01129-7

Reference yield:

(R)-(Z)-2-[5-(2-hydroxyethylidene)tetrahydropyran-2-yl]propan-2-ol (209474-16-8) → (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran (337971-11-6)

Guidance literature:

Multi-step reaction with 5 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

With dmap; sodium hydroxide; sodium hydride; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)01129-7

Reference yield:

(R)-(Z)-2-[2-(2,2,5,5-tetramethyl[1,3]dioxolan-4-yl)ethyl]but-2-ene-1,4-diol (209474-15-7) → (2R,2'RS)-(5Z)-5-[2''-(4'''-methoxybenzyloxy)ethylidene]-2-(2'-methyloxiranyl)tetrahydropyran (337971-11-6)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; dmap; sodium hydroxide; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)01129-7

upstream raw materials:

p-methoxybenzyl chloride

(6'R,1''RS)-(2Z)-2-[6'-(1''-methyloxiranyl)tetrahydropyran-3'-ylidene]ethanol

(R)-(Z)-2-[5-(2-hydroxyethylidene)tetrahydropyran-2-yl]propan-2-ol

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

Downstream raw materials:

(R)-(5'Z)-triisopropyl{2-[5'-[2''-(4'''-methoxybenzyloxy)ethylidene]tetrahydropyran-2'-yl]allyloxy}silane

Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane

(2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane

Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-5,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane