(Z)-5-{(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}-pent-3-en-1-ol

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Chemical Name:(Z)-5-{(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}-pent-3-en-1-ol
CAS No.:104153-89-1
Molecular Formula:C₂₇H₃₈O₄
Molecular Weight:426.596
Hs Code.:

Synonyms:(Z)-5-{(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}-pent-3-en-1-ol

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Chemical Property of (Z)-5-{(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}-pent-3-en-1-ol

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Technology Process of (Z)-5-{(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}-pent-3-en-1-ol

There total 4 articles about (Z)-5-{(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}-pent-3-en-1-ol 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)-5-{(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}-pent-3-enoic acid methyl ester

: 104153-89-1
(Z)-5-{(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}-pent-3-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 2h;
DOI:10.1021/jm00168a032

Reference yield:

: 126451-84-1
1S-<1α,2α,3α(E,3S^*,4R^*),4α>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>acetaldehyde

: 104153-89-1
(Z)-5-{(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}-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 43 percent / methanol / 5 h / 25 °C

2: 94 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 2 h / -78 °C

With diisobutylaluminium hydride; In tetrahydrofuran; methanol; toluene;
DOI:10.1021/jm00168a032

Reference yield:

: 5,6-Dihydroxy-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}-heptanoic acid

: 104153-89-1
(Z)-5-{(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}-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: diethyl ether

2: sodium metaperiodate / methanol; H₂O / 2 h / 25 °C

3: 43 percent / methanol / 5 h / 25 °C

4: 94 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 2 h / -78 °C

With sodium periodate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; water; toluene;
DOI:10.1021/jm00168a032