(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Base Information

Chemical Name:(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester
CAS No.:951378-02-2
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

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Chemical Property of (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

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Technology Process of (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

There total 12 articles about (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester 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: 97.0%

: 289030-99-5
Oleocanthal

: 951378-02-2
(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;
DOI:10.1021/jo071146k

Reference yield:

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 951378-02-2
(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

2: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

3: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran

6: aq. HCl / acetonitrile; H₂O / 0.75 h / 23 °C

7: 66 mg / NaIO₄ / tetrahydrofuran; H₂O / 0.75 h / 0 - 23 °C

8: 97 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; acetonitrile; 3: Wittig reaction / 5: Mitsunobu reaction;
DOI:10.1021/jo071146k

Reference yield:

: 683276-43-9
(4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol

: 951378-02-2
(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: Grubbs catalyst / CH₂Cl₂ / 4 h / 23 °C

1.2: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 12 h / 23 °C

2.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C

3.1: 57 percent / LHMDS; HMPA; Me₂Zn / tetrahydrofuran; toluene / -78 - -45 °C

4.1: KHMDS; CeCl₃ / tetrahydrofuran / -45 °C

5.1: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

6.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran

7.1: aq. HCl / acetonitrile; H₂O / 0.75 h / 23 °C

8.1: 66 mg / NaIO₄ / tetrahydrofuran; H₂O / 0.75 h / 0 - 23 °C

9.1: 97 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; hydrogen; dimethyl zinc(II); potassium hexamethylsilazane; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 4.1: Wittig reaction / 6.1: Mitsunobu reaction;
DOI:10.1021/jo071146k