(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

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Chemical Name:(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal
CAS No.:67040-02-2
Molecular Formula:C₃₃H₄₆O₈
Molecular Weight:570.723
Hs Code.:

Synonyms:(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

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Chemical Property of (E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

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Technology Process of (E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

There total 9 articles about (E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal 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:

: 67040-01-1
(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-prop-2-en-1-ol

: 67040-02-2
(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

Guidance literature:: With manganese(IV) oxide; In dichloromethane; at 25 ℃; for 2h; Yield given;
DOI:10.1021/jm00179a011

Reference yield:

: 65469-92-3
(4aR,5R,6R,7aS)-5-((E)-3-Hydroxy-4-phenoxy-but-1-enyl)-octahydro-cyclopenta[b]pyran-2,6-diol

: 67040-02-2
(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

Guidance literature:: Multi-step reaction with 7 steps

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

2: diethyl ether; ethyl acetate / 5 °C

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

4: 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

5: 35percent H₂O₂ / ethyl acetate; tetrahydrofuran / 0.08 h / 35 °C

6: DIBAL / toluene / 0.17 h / -78 °C

7: MnO₂ / CH₂Cl₂ / 2 h / 25 °C

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

Reference yield:

: 3-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-3-hydroxy-4-phenoxy-but-1-enyl)-cyclopentyl]-propionic acid

: 67040-02-2
(E)-3-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propenal

Guidance literature:: Multi-step reaction with 6 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

With 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