4,5-Heptadienoic acid,7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-,methyl ester, (4R)- (9CI)

Base Information

Chemical Name:4,5-Heptadienoic acid,7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-,methyl ester, (4R)- (9CI)
CAS No.:105368-46-5
Molecular Formula:C₂₃H₂₈O₆
Molecular Weight:400.472
Hs Code.:

Synonyms:4,5-Heptadienoicacid, 7-[3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl]-, methylester, [1S-[1a(S*),2b(1E,3R*),3a]]-; RS 86812-008

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Chemical Property of 4,5-Heptadienoic acid,7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-,methyl ester, (4R)- (9CI)

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Technology Process of 4,5-Heptadienoic acid,7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-,methyl ester, (4R)- (9CI)

There total 17 articles about 4,5-Heptadienoic acid,7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxocyclopentyl]-,methyl ester, (4R)- (9CI) 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: 67.0%

: methyl 11α,15α-bis(tetrahydropyran-2-yloxy)-16-phenoxy-9-oxo-17,18,19,20-tetranorprosta-4,5,13(E)-trienoate

: 73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8
(dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester

Guidance literature:: With water; acetic acid; In tetrahydrofuran; at 40 ℃; for 14h;
DOI:10.1055/s-1994-25576

Reference yield: 67.0%

: 157543-66-3
(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

: 73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8
(dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester

Guidance literature:: With pyridine; hydrogen fluoride; In acetonitrile; for 3h;
DOI:10.1021/jo00066a020

Reference yield:

: 286840-19-5
(3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

: 73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8
(dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / tetrahydrofuran / 5 h / Ambient temperature

2: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

3: 76 percent / CuI*P(OEt)3 / tetrahydrofuran / -40 deg C then 0 deg C, 2 h

4: TBAF / tetrahydrofuran / 3 h / Ambient temperature

5: K₂CO₃ / methanol / 5 h / Ambient temperature

6: pyridinium dichromate / CH₂Cl₂ / 24 h / Ambient temperature

7: pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

8: 67 percent / AcOH, H₂O / tetrahydrofuran / 14 h / 40 °C

With dmap; dipyridinium dichromate; triethylphosphite copper(I) iodide complex; tetrabutyl ammonium fluoride; water; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-1994-25576