1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

Base Information

Chemical Name:1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate
CAS No.:620987-64-6
Molecular Formula:C₂₁H₂₅NO₄
Molecular Weight:355.434
Hs Code.:

Synonyms:1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

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Chemical Property of 1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

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Technology Process of 1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

There total 12 articles about 1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate 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: 98.0%

: 16640-68-9
cyanomethylene triphenylphosphorane

: 620987-56-6
(3R,5R)-5-((1S)-1-methylbut-3-enyl)-2-hydroxyoxolan-3-yl 6-hydroxy-2-prop-2-enylbenzoate

: 620987-64-6
1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

Guidance literature:: In toluene; at 75 ℃; for 1h;
DOI:10.1021/ol035630v

Reference yield:

: 73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6
L-rhamnose

: 620987-64-6
1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / BaCO₃; Br₂ / H₂O / 24 h / 20 °C

2.1: 99 percent / pyridine / 0 - 20 °C

3.1: 99 percent / H₂; Et₃N / Pd/C / ethyl acetate / 24 h / 20 °C / 2585.74 Torr

4.1: NaOMe / methanol / 3 h / 20 °C

4.2: 87 percent / H₂SO₄ / dioxane / 1 h / 20 °C

5.1: 90 percent / EDCI; DMAP / CH₂Cl₂ / 24 h / 20 °C

6.1: DIBAL-H / toluene / 0.25 h / -78 °C

7.1: HCl / dioxane / 4 h / 20 °C

8.1: pyridine / 0.25 h / 0 °C

9.1: -78 °C

10.1: 72 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

11.1: 98 percent / toluene / 1 h / 75 °C

With pyridine; hydrogenchloride; dmap; hydrogen; bromine; sodium methylate; boron trichloride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; barium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; toluene; 11.1: Wittig olefination;
DOI:10.1021/ol035630v

Reference yield:

: 81644-86-2
2,3,5-tri-O-benzoyl-L-rhamnono-1,4-lactone

: 620987-64-6
1-((1E)-2-cyanovinyl)-(1R,3R,4S)-3-hydroxy-4-methylhept-6-enyl 6-hydroxy-2-prop-2-enylbenzoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / H₂; Et₃N / Pd/C / ethyl acetate / 24 h / 20 °C / 2585.74 Torr

2.1: NaOMe / methanol / 3 h / 20 °C

2.2: 87 percent / H₂SO₄ / dioxane / 1 h / 20 °C

3.1: 90 percent / EDCI; DMAP / CH₂Cl₂ / 24 h / 20 °C

4.1: DIBAL-H / toluene / 0.25 h / -78 °C

5.1: HCl / dioxane / 4 h / 20 °C

6.1: pyridine / 0.25 h / 0 °C

7.1: -78 °C

8.1: 72 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 98 percent / toluene / 1 h / 75 °C

With pyridine; hydrogenchloride; dmap; hydrogen; sodium methylate; boron trichloride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; toluene; 9.1: Wittig olefination;
DOI:10.1021/ol035630v