(3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
• CAS No.: 40834-86-4
• Molecular Formula: C22H26O5
• Molecular Weight: 370.445
• Nikkaji Number: J1.276.770F,J28.200F
• Mol file: 40834-86-4.mol

Synonyms:(1-4)beta-(3'-oxo-octen-1')-5alpha-benzoyloxy-3,3abeta,4,5,6,6abeta-hexahydro-2H-cyclopenta(b)furan-2-one;5-(benzoyloxy)-3,3a,4,5,6,6a-hexahydro-4-(3-oxo-1-octenyl)-2H-cyclopenta(b)furan-2-one;BHOOCFO

Chemical Property of (3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Chemical Property:

• Refractive Index: 1.554
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 238.3 °C
• PSA: 69.67000
• Density: 1.18 g/cm³
• LogP: 3.86920
• Storage Temp.: 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 370.17802393
• Heavy Atom Count: 27
• Complexity: 575

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-ylbenzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC1C(CC2C1CC(=O)O2)OC(=O)C3=CC=CC=C3
• Isomeric SMILES: CCCCCC(=O)/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC(=O)C3=CC=CC=C3

Technology Process of (3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

There total 9 articles about (3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxooct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 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: 96.0%

2-oxohexylphosphonic acid dimethyl ester (61728-15-2) + (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester (40834-86-4,185225-06-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo801190m

Reference yield: 96.0%

dimethyl 2-oxoheptylphosphonate (36969-89-8) + (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (3aR,6aS)-4-((E)-3-Oxo-oct-1-enyl)-3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one (49673-16-7) + (3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester (40834-86-4,185225-06-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.bmcl.2005.02.011

Reference yield: 91.5%

dimethyl 2-oxoheptylphosphonate (36969-89-8) + (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester (40834-86-4,185225-06-3)

Guidance literature:

dimethyl 2-oxoheptylphosphonate; With lithium hydroxide; In tert-butyl methyl ether; at 20 ℃; for 1h;

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one; In tert-butyl methyl ether; water; at 20 ℃; for 1h;

upstream raw materials:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

dimethyl 2-oxoheptylphosphonate

2-oxohexylphosphonic acid dimethyl ester

1-(triphenylphosphoranylidene)-2-heptanone

Downstream raw materials:

(3aR,4R,5R,6aS)-4-((E)-3-hydroxy-3-methyloct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

(3aR,4R,5R,6aS)-4-((E)-3,3-difluorooct-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

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

(5Z)-7-{(1RS,2SR,5RS)-2-[(1E,3SR)-3-(tert-butyldimethylsilanyloxy)oct-1-enyl]-5-(2-nitrophenylselanyl)cyclopent-3-enyl}hept-5-enoic acid methyl ester

Refernces

• 1、 -. "PROSTAGLANDIN E1 AND E2 ANALOGS FOR THE TREATMENT OF VARIOUS MEDICAL CONDITIONS". Page/Page column 7. . Retrieved 2009/05/28.
• 2、 -. "Method for preparing prostaglandin derivative". Page/Page column 14-15. . Retrieved 2010/11/28.