(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

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Chemical Name:(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate
CAS No.:550316-67-1
Molecular Formula:C₂₀H₂₆O₄
Molecular Weight:330.424
Hs Code.:

Synonyms:(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

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Technology Process of (2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

There total 6 articles about (2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate 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%

: 550316-66-0
(2R,3S,4R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-4-phenoxythiocarbonyloxy-tetrahydrofuran-3-yl benzoate

: 550316-67-1
(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Heating;
DOI:10.1016/S0957-4166(03)00078-8

Reference yield:

: 7284-07-3
5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose

: 550316-67-1
(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / CuCl; oxygen / PdCl₂ / dimethylformamide; H₂O / 4 h / 20 °C

2: 85 percent / KN(TMS)2 / tetrahydrofuran; toluene / 2 h / -20 °C

3: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

4: 89 percent / acetyl chloride / 12 h / Heating

5: 95 percent / 4-(N,N-dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h / 0 °C

6: 78 percent / tri-n-butyltin hydride; 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); oxygen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; acetyl chloride; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Wacker oxidation / 2: Wittig reaction;
DOI:10.1016/S0957-4166(03)00078-8

Reference yield:

: 96687-98-8
[3aR,4aR,7aS,7bR]-2,2-dimethylperhydrofuro[2,3:4,5]furo[2,3-d][1,3]dioxol-6(R/S)-ol

: 550316-67-1
(2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / KN(TMS)2 / tetrahydrofuran; toluene / 2 h / -20 °C

2: 95 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

3: 89 percent / acetyl chloride / 12 h / Heating

4: 95 percent / 4-(N,N-dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h / 0 °C

5: 78 percent / tri-n-butyltin hydride; 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hexamethylsilazane; acetyl chloride; In tetrahydrofuran; dichloromethane; toluene; 1: Wittig reaction;
DOI:10.1016/S0957-4166(03)00078-8