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

Base Information

• Chemical Name: <1S<1α,2α(2E,5E),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic acid
• CAS No.: 100827-74-5
• Molecular Formula: C₂₄H₃₀O₄
• Molecular Weight: 382.5

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 8 articles about <1S<1α,2α(2E,5E),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic 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: 83.0%

(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 (100827-73-4) → <1S<1α,2α(2E,5E),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic acid (100827-74-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃; for 18h;

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(2E,5E),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic acid (100827-74-5)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 80 percent / 30percent aq. H₂O₂ / tetrahydrofuran / 1 h / 25 °C

4: 83 percent / 2 N aq. HCl / tetrahydrofuran / 18 h / 25 °C

With hydrogenchloride; lithium hydroxide; dihydrogen peroxide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jm00168a032

Reference yield:

(Z)-2-Phenylselanyl-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 (100827-72-3,126451-89-6,126451-93-2) → <1S<1α,2α(2E,5E),3α(E,3S*,4R*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic acid (100827-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 30percent aq. H₂O₂ / tetrahydrofuran / 1 h / 25 °C

2: 83 percent / 2 N aq. HCl / tetrahydrofuran / 18 h / 25 °C

With hydrogenchloride; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1021/jm00168a032

upstream raw materials:

(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 <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)-2-Phenylselanyl-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

(Z)-2-Phenylselanyl-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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