Corey PG-lactone diol

Base Information

• Chemical Name: Corey PG-lactone diol
• CAS No.: 39182-59-7
• Molecular Formula: C15H24O4
• Molecular Weight: 268.353
• Mol file: 39182-59-7.mol

Synonyms:2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-(3-hydroxy-1-octenyl)-, [3aR-[3aa,4a(1E,3R*),5b,6aa]]-;2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-1-octenyl]-, (3aR,4R,5R,6aS)- (9CI);Corey PG-lactone diol;

Chemical Property of Corey PG-lactone diol

Chemical Property:

• Vapor Pressure: 3.35E-09mmHg at 25°C
• Refractive Index: 1.576
• Boiling Point: 430.072 °C at 760 mmHg
• PKA: 14.30±0.40(Predicted)
• Flash Point: 156.399 °C
• PSA: 66.76000
• Density: 1.199 g/cm³
• LogP: 1.79630

Purity/Quality:

99%, ^*data from raw suppliers

COREYPG-LACTONEDIOL 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Corey PG-lactone diol

There total 66 articles about Corey PG-lactone diol 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: 76.0%

[3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one (51705-58-9) → (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (39182-59-7)

Guidance literature:

With potassium carbonate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1039/a804276d

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

upstream raw materials:

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

[3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one

(Z)-(1S,5R,6R,7R,1'R)-7-Benzoyloxy-6-(1'-hydroxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one

(Z)-(1S,5R,6R,7R,1'S)-7-Benzoyloxy-6-(1'-hydroxyoct-2'-enyl)-2-oxabicyclo[3.3.0]octan-3-one

Downstream raw materials:

(3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-trimethylsilanylethynyl-hexahydro-cyclopenta[b]pyrrol-2-one

(3aR,4R,5R,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-1-(2,4-dimethoxy-benzyl)-6a-prop-1-ynyl-hexahydro-cyclopenta[b]pyrrol-2-one

(3aR,4R,5R,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-6a-phenylsulfanyl-hexahydro-cyclopenta[b]pyrrol-2-one

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

Refernces

• 1、 Fleming, Ian,Winter, Stephen B. D.. "Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of prostaglandins controlling the stereochemistry at C-15 using a silyl-to-hydroxy conversion following a stereochemically convergent synthesis of an allylsilane". . p. 2687 - 2700. Retrieved 2007/10/03.
• 2、 Mahrwald, Rainer,Schick, Hans,Pivnitsky, Kasimir K.,Schwarz, Sigfrid. "Prostaglandins and Prostaglandin Intermediates. Part 26 A Novel Route to PGF2α using Triisopropoxy-hept-1-ynyl-titanium as Precursor for the β-Side Chain". . p. 403 - 413. Retrieved 2007/10/02.