3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

Base Information

Chemical Name:3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid
CAS No.:73319-03-6
Molecular Formula:C₁₈H₂₃ClO₆
Molecular Weight:370.83
Hs Code.:

Synonyms:3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

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Chemical Property of 3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

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Technology Process of 3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

There total 2 articles about 3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid 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:

: 67039-85-4
2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol

: 73319-03-6
3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

Guidance literature:: With sodium hydroxide; silver nitrate; In methanol; at 25 ℃; for 2h;
DOI:10.1021/jm00179a011

Reference yield:

: 67039-82-1
2-syn-(3-methoxy-trans,cis-propenyl)-3-anti-<3αβ-(tetrahydropyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol

: 73319-03-6
3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 58 percent / 65percent aq. acetic acid / tetrahydrofuran / 3 h / 60 °C

2: aq. AgNO₃, aq. NaOH / methanol / 2 h / 25 °C

With sodium hydroxide; silver nitrate; acetic acid; In tetrahydrofuran; methanol;
DOI:10.1021/jm00179a011

Reference yield:

: 73319-03-6
3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

: 73307-40-1
(2E,4E,6E)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-hepta-2,4,6-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: diethyl ether; ethyl acetate / 5 °C

2: p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 10 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 40 min, b) 5 deg C, 30 min

4: 35percent H₂O₂ / ethyl acetate; tetrahydrofuran / 0.08 h / 35 °C

5: DIBAL / toluene / 0.17 h / -78 °C

6: MnO₂ / CH₂Cl₂ / 2 h / 25 °C

7: CH₂Cl₂ / 12 h / Heating

8: 1 N aq. HCl / tetrahydrofuran / 1 h / 45 °C

With hydrogenchloride; manganese(IV) oxide; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jm00179a011