PGE1 alcohol

Base Information

• Chemical Name: PGE1 alcohol
• CAS No.: 21562-57-2
• Molecular Formula: C20H36O4
• Molecular Weight: 340.4974
• DSSTox Substance ID: DTXSID201234163
• Nikkaji Number: J395.285A
• Wikidata: Q76286278
• Metabolomics Workbench ID: 2414
• Mol file: 21562-57-2.mol

Synonyms:1-decarboxy-1-hydroxymethyl-PGE1;1-decarboxy-1-hydroxymethylprostaglandin E1;2-decarboxy-2-hydroxymethylprostaglandin E1;PGE1-carbinol;TR 4161;TR-4161;TR4161

Chemical Property of PGE1 alcohol

Chemical Property:

• Vapor Pressure: 1.27E-11mmHg at 25°C
• Boiling Point: 489.2°Cat760mmHg
• PKA: 13.85±0.60(Predicted)
• Flash Point: 263.7°C
• PSA: 77.76000
• Density: 1.077g/cm³
• LogP: 3.38280
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 340.26135963
• Heavy Atom Count: 24
• Complexity: 367

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin E1 Alcohol ≥99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CCCCCCCO)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCCO)O)O

Technology Process of PGE1 alcohol

There total 19 articles about PGE1 alcohol 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: 90.0%

(2S,3S,4S)-3-[(E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4-hydroxy-2-(7-hydroxy-heptyl)-cyclopentanone (93566-57-5,93566-58-6,93711-57-0,93711-58-1,110548-24-8) → (+/-)-2-decarboxy-2-(hydroxymethyl)prostaglandin E1 (21562-57-2,93566-59-7)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo00231a014

Reference yield:

6-oxabicyclo<3.1.0>hex-2-ene (7129-41-1,54460-11-6) → (+/-)-2-decarboxy-2-(hydroxymethyl)prostaglandin E1 (21562-57-2,93566-59-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CuCN, / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -40 deg C to r.t., 7 h

2: 98 percent / tert-butylhydroperoxide / vanadyl acetylacetonate / benzene / 24 h / 40 °C

3: 82 percent / CrO₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h

5: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

6: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

7: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With chromium(VI) oxide; tert.-butylhydroperoxide; potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; lithium diisopropyl amide; vanadyl acetylacetonate; In ethanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/jo00231a014

Reference yield:

(1S*,4S*,1'E)-4-[{3'-(tert-butyldimethylsilyl)oxy}-1'-octenyl]-2-cyclopenten-1-ol (78823-17-3) → (+/-)-2-decarboxy-2-(hydroxymethyl)prostaglandin E1 (21562-57-2,93566-59-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / tert-butylhydroperoxide / vanadyl acetylacetonate / benzene / 24 h / 40 °C

2: 82 percent / CrO₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h

4: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

5: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

6: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With chromium(VI) oxide; tert.-butylhydroperoxide; potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; lithium diisopropyl amide; vanadyl acetylacetonate; In ethanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/jo00231a014

upstream raw materials:

(4R)-4-hydroxy-2-(7-hydroxyheptyl)cyclopent-2-enone

8-(2-methyl-[1,3]dioxolan-2-yl)-octanoic acid ethyl ester

10-hydroxy-2-decanone

(R)-4-Hydroxy-2-(7-hydroxy-heptyl)-cyclopentane-1,3-dione

Refernces

• 1、 Marino, Joseph P.,Pradilla, Roberto Fernandez de la,Laborde, Edgardo. "Stereocontrolled Synthesis of Prostaglandins from Cyclopentadiene Monoepoxide". . p. 5279 - 5280. Retrieved 2007/10/02.