(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

Base Information

Chemical Name:(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol
CAS No.:87692-44-2
Molecular Formula:C₂₃H₃₄O₄
Molecular Weight:374.521
Hs Code.:

Synonyms:(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

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Chemical Property of (1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

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Technology Process of (1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

There total 9 articles about (1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol 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: 57.0%

: 87692-43-1
(1S,3R,4R,5R)-4-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

: 87692-44-2
(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 48 ℃; for 14h;

Reference yield:

: 13345-50-1
prostaglandin A₂

: 87692-44-2
(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

Guidance literature:: Multi-step reaction with 9 steps

1: diethyl ether / 0.5 h / 0 - 5 °C

2: imidazole / dimethylformamide / 2 h / Ambient temperature

3: 95 percent / 30percent hydrogen peroxide, 3 M aq. lithium hydroxide / methanol / 5 h / -30 - -25 °C

4: aq. sodium hydrogen carbonate, aluminium amalgam / tetrahydrofuran; methanol / 1.) 10 deg C, 2 h, 2.) room temperature, 4 h

5: 80 percent / K-Selectride / tetrahydrofuran / 5 h / -50 - -45 °C

6: 65 percent / N-methylmorpholine N-oxide dihydrate, water, osmium tetraoxide / 2-methyl-propan-2-ol; acetone / 0.67 h

7: 70 percent / sodium metaperiodate / H₂O; dioxane / 8.5 h / Ambient temperature

8: sodium methylsulphinylmethanide / 1.) DMSO, 20 deg C, 30 min, 2.) room temperature, 36 h

9: 57 percent / tetrabutylammonium fluoride / tetrahydrofuran / 14 h / 48 °C

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; aluminium amalgam; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hydrogencarbonate; sodium methylsulfinylmethanide; potassium tri-sec-butyl-borohydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

Reference yield:

: 31753-19-2
(5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid

: 87692-44-2
(1S,3R,4R,5R)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-[(Z)-3-(4-methoxy-phenyl)-allyl]-cyclopentane-1,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 2 h / Ambient temperature

2: 95 percent / 30percent hydrogen peroxide, 3 M aq. lithium hydroxide / methanol / 5 h / -30 - -25 °C

3: aq. sodium hydrogen carbonate, aluminium amalgam / tetrahydrofuran; methanol / 1.) 10 deg C, 2 h, 2.) room temperature, 4 h

4: 80 percent / K-Selectride / tetrahydrofuran / 5 h / -50 - -45 °C

5: 65 percent / N-methylmorpholine N-oxide dihydrate, water, osmium tetraoxide / 2-methyl-propan-2-ol; acetone / 0.67 h

6: 70 percent / sodium metaperiodate / H₂O; dioxane / 8.5 h / Ambient temperature

7: sodium methylsulphinylmethanide / 1.) DMSO, 20 deg C, 30 min, 2.) room temperature, 36 h

8: 57 percent / tetrabutylammonium fluoride / tetrahydrofuran / 14 h / 48 °C

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; aluminium amalgam; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hydrogencarbonate; sodium methylsulfinylmethanide; potassium tri-sec-butyl-borohydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;