(3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(3-oxo-1-octen-1-yl)-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(3-oxo-1-octen-1-yl)-2H-cyclopenta[b]furan-2-one
• CAS No.: 185225-06-3
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 185225-06-3.mol

Synonyms:2H-Cyclopenta[b]furan-2-one,5-(benzoyloxy)hexahydro-4-(3-oxo-1-octenyl)-, [3aR-(3aa,4a,5b,6aa)]- (9CI)

Chemical Property of (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(3-oxo-1-octen-1-yl)-2H-cyclopenta[b]furan-2-one

Chemical Property:

• Vapor Pressure: 5.2E-12mmHg at 25°C
• Boiling Point: 546.8oC at 760 mmHg
• Flash Point: 238.3oC
• PSA: 69.67000
• Density: 1.18
• LogP: 3.86920

Purity/Quality:

98% or more ^*data from raw suppliers

(3AR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(3-oxo-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:

Technology Process of (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(3-oxo-1-octen-1-yl)-2H-cyclopenta[b]furan-2-one

There total 12 articles about (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(3-oxo-1-octen-1-yl)-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: 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:

n-pentyl methyl ketone

Benzoic acid (3aR,4R,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

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

dimethyl 2-oxoheptylphosphonate

Downstream raw materials:

(15R)-PGE2

prostaglandin J₂