(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

Base Information

Chemical Name:(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate
CAS No.:550316-65-9
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

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Chemical Property of (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

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Technology Process of (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

There total 4 articles about (2R,3R,4R)-4-hydroxy-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: 89.0%

: 67-56-1
methanol

: 550316-64-8
(3aR,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl benzoate

: 550316-65-9
(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

Guidance literature:: With acetyl chloride; for 12h; 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

: 550316-65-9
(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 4 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

With pyridine; oxygen; 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

: 550316-65-9
(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 3 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

With pyridine; potassium hexamethylsilazane; acetyl chloride; In tetrahydrofuran; dichloromethane; toluene; 1: Wittig reaction;
DOI:10.1016/S0957-4166(03)00078-8