<1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid

Base Information

• Chemical Name: <1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid
• CAS No.: 126295-63-4
• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.543

Synonyms:<1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid

Chemical Property of <1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of <1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid

There total 9 articles about <1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic 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: 94.0%

(Z)-7-[(1S,2R,3S,4R)-3-((E)-(3R,4S)-3-Hydroxy-4-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-3-methyl-hept-5-enoic acid methyl ester (126295-72-5) → <1S<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid (126295-63-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 25 ℃; for 96h;

DOI:10.1021/jm00168a032

Reference yield:

methyl <1S-<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (101399-94-4) → <1S<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid (126295-63-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium diisopropylamide / 1.) THF/hexane, -78 deg C, 30 min, 2.) -78 deg C, 30 min

2: 71 percent / 30percent aq. H₂O₂ / tetrahydrofuran; methanol / 1.) 0-5 deg C, 30 min, 2.) 25 deg C, 1 h

3: 1.) cuprous iodide / 1.) ether, 0 deg C, 30 min, 2.) -20 deg C, 1 h

4: 96 percent / Amberlyst-15 resin / methanol / 18 h / 25 °C

5: 94 percent / 1 N aq. LiOH / tetrahydrofuran / 96 h / 25 °C

With lithium hydroxide; copper(l) iodide; amberlyst-15 resin; dihydrogen peroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1021/jm00168a032

Reference yield:

(Z)-3-Methyl-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hept-5-enoic acid methyl ester (126295-69-0) → <1S<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid (126295-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Amberlyst-15 resin / methanol / 18 h / 25 °C

2: 94 percent / 1 N aq. LiOH / tetrahydrofuran / 96 h / 25 °C

With lithium hydroxide; amberlyst-15 resin; In tetrahydrofuran; methanol;

DOI:10.1021/jm00168a032

upstream raw materials:

(Z)-7-[(1S,2R,3S,4R)-3-((E)-(3R,4S)-3-Hydroxy-4-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-3-methyl-hept-5-enoic acid methyl ester

(2E,5Z)-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hepta-2,5-dienoic acid methyl ester

methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

(Z)-3-Methyl-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hept-5-enoic acid methyl ester

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