1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

Base Information

• Chemical Name: 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane
• CAS No.: 67039-91-2
• Molecular Formula: C₄₀H₅₃ClO₉Se
• Molecular Weight: 792.268

Synonyms:1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

Chemical Property of 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

There total 5 articles about 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane 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:

2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol (67039-85-4) → 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane (67039-91-2)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm00179a011

Reference yield:

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid (73319-03-6) → 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane (67039-91-2)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jm00179a011

Reference yield:

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid methyl ester (67039-86-5,109429-57-4) → 1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-<2-carbomethoxy-2-(phenylselenyl)ethyl>-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane (67039-91-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 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

With toluene-4-sulfonic acid; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jm00179a011

upstream raw materials:

diphenyl diselenide

1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-(2-carbomethoxyethyl)-3-anti-<3αβ-(tetrahydrppyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

Downstream raw materials:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F_1α methyl ester

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

(2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-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

1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-(2-formyl-1-trans-ethenyl)-3-anti-<3αβ-(tetrahydropyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

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