(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]-acrylic acid methyl ester

Base Information

• 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]-acrylic acid methyl ester
• CAS No.: 67040-00-0
• Molecular Formula: C₃₄H₄₈O₉
• Molecular Weight: 600.75

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]-acrylic acid methyl ester

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]-acrylic acid methyl ester

Chemical Property:

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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]-acrylic acid methyl ester

There total 7 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]-acrylic 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:

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]-2-phenylselanyl-propionic acid methyl ester (67039-99-0) → (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]-acrylic acid methyl ester (67040-00-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; ethyl acetate; at 35 ℃; for 0.0833333h;

DOI:10.1021/jm00179a011

Reference yield:

(4aR,5R,6R,7aS)-5-((E)-3-Hydroxy-4-phenoxy-but-1-enyl)-octahydro-cyclopenta[b]pyran-2,6-diol (65469-92-3) → (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]-acrylic acid methyl ester (67040-00-0)

Guidance literature:

Multi-step reaction with 5 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

With sodium hydroxide; dihydrogen peroxide; toluene-4-sulfonic acid; silver nitrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;

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 → (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]-acrylic acid methyl ester (67040-00-0)

Guidance literature:

Multi-step reaction with 4 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

With dihydrogen peroxide; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

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]-2-phenylselanyl-propionic acid methyl ester

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

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

2-oxa-6-syn-<3αβ-(tetrahydropyran-2-yloxy)-4-phenoxy-1-trans-butenyl>-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-ol

Downstream raw materials:

16-phenoxy-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexahydroprostaglandin F_1α methyl ester

(2E,4E,6E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-4-phenoxy-but-1-enyl)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

(2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

(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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