D17 Prostaglandin E1

Base Information

• Chemical Name: D17 Prostaglandin E1
• CAS No.: 7046-45-9
• Molecular Formula: C20H32O5
• Molecular Weight: 352.47
• Nikkaji Number: J562.735D
• Metabolomics Workbench ID: 2485
• Mol file: 7046-45-9.mol

Synonyms:17,18-dehydro-PGE1;17,18-dehydroprostaglandin E1;5,6-dihydro-PGE3;5,6-dihydroprostaglandin E3

Chemical Property of D17 Prostaglandin E1

Chemical Property:

• PSA: 94.83000
• LogP: 3.25110
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

98%Min ^*data from raw suppliers

delta17-ProstaglandinE1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
• Isomeric SMILES: CC/C=C\C[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O

Technology Process of D17 Prostaglandin E1

There total 6 articles about D17 Prostaglandin E1 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: 89.0%

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(1E,5Z)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-octa-1,5-dienyl]-5-oxo-cyclopentyl}-heptanoic acid (127269-01-6) → 7-[(1R,2R,3R)-3-Hydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-5-oxo-cyclopentyl]-heptanoic acid (7046-45-9)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99365-1

Reference yield:

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6) → 7-[(1R,2R,3R)-3-Hydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-5-oxo-cyclopentyl]-heptanoic acid (7046-45-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi, (2-thienyl)Cu(CN)Li / 1.) THF, -78 deg C; 2.) THF, -78 to 0 deg C, 1 h

2: 76 percent / (2-thienyl)Cu(CN)Li / tetrahydrofuran / -78 deg C up to 0 deg C

3: 87 percent / PPTS / propan-2-ol; diethyl ether / 5 h / Ambient temperature

4: 91 percent / Jones reagent / acetone; diethyl ether / 0.5 h / 0 °C

5: 89 percent / aq. HF / acetonitrile / 0.67 h / Ambient temperature

With n-butyllithium; jones reagent; hydrogen fluoride; thien-2-yl(cyano)copper lithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; isopropyl alcohol; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)99365-1

Reference yield:

tert-Butyl-dimethyl-[(Z)-(S)-1-((E)-2-tributylstannanyl-vinyl)-hex-3-enyloxy]-silane (127268-93-3) → 7-[(1R,2R,3R)-3-Hydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-5-oxo-cyclopentyl]-heptanoic acid (7046-45-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi, (2-thienyl)Cu(CN)Li / 1.) THF, -78 deg C; 2.) THF, -78 to 0 deg C, 1 h

2: 76 percent / (2-thienyl)Cu(CN)Li / tetrahydrofuran / -78 deg C up to 0 deg C

3: 87 percent / PPTS / propan-2-ol; diethyl ether / 5 h / Ambient temperature

4: 91 percent / Jones reagent / acetone; diethyl ether / 0.5 h / 0 °C

5: 89 percent / aq. HF / acetonitrile / 0.67 h / Ambient temperature

With n-butyllithium; jones reagent; hydrogen fluoride; thien-2-yl(cyano)copper lithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; isopropyl alcohol; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)99365-1

upstream raw materials:

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(1E,5Z)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-octa-1,5-dienyl]-5-oxo-cyclopentyl}-heptanoic acid

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol

tert-Butyl-dimethyl-[(Z)-(S)-1-((E)-2-tributylstannanyl-vinyl)-hex-3-enyloxy]-silane

(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-[(1E,5Z)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-octa-1,5-dienyl]-2-methylene-cyclopentanone

Refernces