(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

Base Information

Chemical Name:(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
CAS No.:100827-69-8
Molecular Formula:C₃₀H₄₀O₅
Molecular Weight:480.645
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 71.0%

: 100827-68-7,126451-83-0,126451-90-9
(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

: 100827-69-8
(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

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran; methanol; 1.) 0-5 deg C, 30 min, 2.) 25 deg C, 1 h;
DOI:10.1021/jm00168a032

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 100827-69-8
(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

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.67 h / 0 - 5 °C

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

3: 71 percent / 30percent aq. H₂O₂ / tetrahydrofuran; methanol / 1.) 0-5 deg C, 30 min, 2.) 25 deg C, 1 h

With dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm00168a032

Reference yield:

: 101399-94-4
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

: 100827-69-8
(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

Guidance literature:: Multi-step reaction with 2 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

With dihydrogen peroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol;
DOI:10.1021/jm00168a032