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

Base Information

Chemical Name:(5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic Acid Methyl Ester
CAS No.:62092-49-3
Molecular Formula:C₃₈H₅₆O₉
Molecular Weight:656.857
Hs Code.:

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

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

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

There total 9 articles about (5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic 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:

: 110-87-2
3,4-dihydro-2H-pyran

: 62524-92-9
(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

: 62092-49-3
(5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic Acid Methyl Ester

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 0.333333h; Yield given;
DOI:10.1021/jm00179a011

Reference yield:

: 40665-68-7
dimethyl (3-phenoxy-2-oxopropyl)phosphonate

: 62092-49-3
(5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic Acid Methyl Ester

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm00179a011

Reference yield:

: 61218-06-2
methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

: 62092-49-3
(5Z,13E)-(8R,9S,11R,12R,15R)-16-Phenoxy-9,11,15-tris(tetrahydropyran-2-yloxy)-17,18,19,20-tetranorprostadienoic Acid Methyl Ester

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm00179a011