7-[3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-[4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]cyclopentyl]-2-phenylseleno-5-heptenoic acid methyl ester

Base Information

• Chemical Name: 7-[3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-[4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]cyclopentyl]-2-phenylseleno-5-heptenoic acid methyl ester
• CAS No.: 62524-93-0
• Molecular Formula: C44H60O9Se
• Molecular Weight: 811.915
• Mol file: 62524-93-0.mol

Synonyms:

Chemical Property of 7-[3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-[4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]cyclopentyl]-2-phenylseleno-5-heptenoic acid methyl ester

Chemical Property:

• Vapor Pressure: 2.7E-27mmHg at 25°C
• Boiling Point: 824.3°Cat760mmHg
• Flash Point: 452.3°C
• PSA: 90.91000
• Density: g/cm³
• LogP: 7.71080

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): A reproductive hazard. TWA 0.2 mg(Se)/m³
• Hazard Codes: A reproductive hazard. TWA 0.2 mg(Se)/m3

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-[3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-[4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]cyclopentyl]-2-phenylseleno-5-heptenoic acid methyl ester

There total 10 articles about 7-[3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-[4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]cyclopentyl]-2-phenylseleno-5-heptenoic 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:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) → (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester (62524-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: 36 percent / NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00179a011

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester (62524-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: 36 percent / NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00179a011

Reference yield:

methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate (61218-10-8) → (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester (62524-93-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / SO₃-pyridine complex, Et₃N / dimethylsulfoxide / 0.25 h / 20 °C

2: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

3: 36 percent / NaBH₄ / methanol; tetrahydrofuran / -45 °C

4: K₂CO₃ / methanol / 1 h / 50 °C

5: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

6: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

With sodium tetrahydroborate; pyridine-SO₃ complex; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm00179a011

upstream raw materials:

diphenyl diselenide

(5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic Acid Methyl Ester

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

Downstream raw materials:

16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

16-phenoxy-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester

16-phenoxy-17,18,19,20-tetranor-2,3-trans-didehydroprostagland

Refernces