(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

Base Information

• Chemical Name: (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
• CAS No.: 177768-48-8
• Molecular Formula: C₂₆H₃₈O₆
• Molecular Weight: 446.584
• Mol file: 177768-48-8.mol

Synonyms:

Chemical Property of (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

There total 5 articles about (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl 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:

(Z)-7-[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester → (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester (177768-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NaHSO₄*H₂O / tetrahydrofuran; H₂O / 13 h / Ambient temperature

2: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl₃, 3.) DIPEA, LiCl, 4.) aq. H₂O₂

3: 1.) CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 1 h

4: 1.) PhB(OH)2, 2.) Ti(OiPr)4, (-)-D-diisopropyl tartrate, 3.) t-BuOOH, 4.) aq. H₂O₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium hydrogen sulfate; aluminium trichloride; cerium(III) chloride; (-)-diisopropyl tartrate; 3 A molecular sieve; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; phenylboronic acid; In tetrahydrofuran; water;

DOI:10.1021/jo960098t

Reference yield:

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130273-87-9) → (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester (177768-48-8) + (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester (177768-49-9)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo960098t

Reference yield:

dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0) → (Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester (177768-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl₃, 3.) DIPEA, LiCl, 4.) aq. H₂O₂

2: 1.) CeCl₃*7H₂O, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 1 h

3: 1.) PhB(OH)2, 2.) Ti(OiPr)4, (-)-D-diisopropyl tartrate, 3.) t-BuOOH, 4.) aq. H₂O₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; aluminium trichloride; cerium(III) chloride; (-)-diisopropyl tartrate; 3 A molecular sieve; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; phenylboronic acid;

DOI:10.1021/jo960098t

upstream raw materials:

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

dimethyl(2-oxo-4-phenylbutyl)phosphonate

15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester