(3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 26054-67-1
• Molecular Formula: C15H24O4
• Molecular Weight: 268.353
• DSSTox Substance ID: DTXSID001114985
• Nikkaji Number: J28.186G,J1.949.570A
• Wikidata: Q76422970
• Mol file: 26054-67-1.mol

Synonyms:26054-67-1;(3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one;Prostaglandin lactone-diol;(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one;(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one;CHEBI:177958;DTXSID001114985;AMY30101;AKOS016004249;AC-28187;PD020854;J-501158;J-700392;(3aR, 4R, 5R, 6aS)-5-hydroxy-4-[(E, 3S)-3-hydroxyoct-1-enyl]-3, 3a, 4, 5, 6, 6a-hexahydrocyclopenta[b]furan-2-one;(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]uran-2-one;2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-, (3aR,4R,5R,6aS)-;2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-,(3aR,4R,5R,6aS)-

Chemical Property of (3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

• Boiling Point: 430.1±45.0 °C(Predicted)
• PKA: 14.30±0.40(Predicted)
• PSA: 66.76000
• Density: 1.199±0.06 g/cm3(Predicted)
• LogP: 1.79630
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 268.16745924
• Heavy Atom Count: 19
• Complexity: 339

Purity/Quality:

97% ^*data from raw suppliers

(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=O)O2)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)O)O
• Uses: (3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.

Technology Process of (3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

There total 55 articles about (3aR,4R,5R,6aS)-5-Hydroxy-4-((S,E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 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: 80.8%

lactone of 5α-hydroxy-3α-(2-tetrahydrofuryloxy)-2β-<3α-(2-tetrahydrofuryloxy)-trans-1-octenyl>cyclopentyl-1α-acetic acid (114951-80-3) → (1SR,5RS,6RS,7RS)-7-hydroxy-6-<(3SR)-3-hydroxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one (23782-33-4,26054-67-1,39182-59-7,39521-48-7,39648-33-4,39648-34-5,42586-67-4,42586-74-3,52992-73-1,53110-06-8,53275-56-2,54383-09-4,58865-62-6,58865-63-7,62929-80-0,62929-81-1,67179-95-7)

Guidance literature:

With Dowex 50 x 2 (H⁽¹⁺⁾) ion-exchange resin; In ethanol; for 1h; Ambient temperature;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (39182-59-7) + (-)-7α-hydroxy-6β-(3α-hydroxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one (26054-67-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: formic acid; sulfuric acid / 24 h / 80 °C

1.2: 2 h / 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / -30 °C

With formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; sulfuric acid; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Corey-Bakshi-Shibata Reduction;

DOI:10.1002/anie.201902371

Reference yield:

trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone (78823-20-8) → (3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (23782-33-4,26054-67-1,39182-59-7,39521-48-7,39648-33-4,39648-34-5,42586-67-4,42586-74-3,52992-73-1,53110-06-8,53275-56-2,54383-09-4,58865-62-6,58865-63-7,62929-80-0,62929-81-1,67179-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1. LDA / 1. THF, -78 deg C;

2: 1. LiAlH₄, 2. i-Pr₂EtN / 1. Et₂O, 2. CH₂Cl₂

3: 70 percent / CuSO₄ / benzene / 90 °C

4: 95 percent / Et₃NF / tetrahydrofuran / Ambient temperature

5: 80 percent / Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride (PBPH) / tetrahydrofuran / a. -78 deg C, b. RT

6: 15percent aq. HF / acetonitrile

7: 5percent HCl / tetrahydrofuran; H₂O

With hydrogenchloride; lithium aluminium tetrahydride; Lithium cis,cis,trans-perhydro-9b-boraphenalyl hydride; hydrogen fluoride; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; copper(II) sulfate; In tetrahydrofuran; water; acetonitrile; benzene;

DOI:10.1021/jo00200a063

upstream raw materials:

(-)-7α-Hydroxy-3-oxo-6β-<3-oxo-1(E)-octenyl>-cis-2-oxabicyclo<3.3.0>octane

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

cyclopenta-1,3-diene

Downstream raw materials:

(3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate

E-(S)-(+)-1-phenyloct-1-en-3-ol

dinoprost

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol