(+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL

Base Information

• Chemical Name: (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL
• CAS No.: 39265-57-1
• Molecular Formula: C21H20O5
• Molecular Weight: 352.387
• Mol file: 39265-57-1.mol

Synonyms:(3aR,4S,5R,6aS)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1'-biphenyl-4-carboxylate;(+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL;(3aS,4R,5S,6aR)-(+)-Hexahydro-4-(hydroxymethyl)-5-(4-phenylbenzoyloxy)cyclopenta[b]-furan-2-one;(3aS,4R,5S,6aR)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzyloxy)cyclopenta[b]furan-2-one;(3aS,4R,5S,6aR)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1'-Biphenyl]-4-carboxylic Acid

Chemical Property of (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL

Chemical Property:

• Vapor Pressure: 1.61E-14mmHg at 25°C
• Melting Point: 134-136 °C(lit.)
• Boiling Point: 584.8°C at 760 mmHg
• Flash Point: 210.6°C
• PSA: 72.83000
• Density: 1.32
• LogP: 2.82290
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(+)-CoreyLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3aS,4R,5S,6aR)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1'-Biphenyl]-4-carboxylic Acid is a corey lactone derivative and a key intermediate in the synthesis of prostaglan dins. (3aS,4R,5S,6aR)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl Ester [1,1''-Biphenyl]-4-carboxylic Acid is a corey lactone derivative and a key intermediate in the synthesis of prostaglandins.

Technology Process of (+)-COREY LACTONE, 4-PHENYLBENZOATE ALCOHOL

There total 7 articles about (+)-COREY LACTONE, 4-PHENYLBENZOATE 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: 94.01%

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → <3aS(3aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one (39265-57-1)

Guidance literature:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one; With pyridine; trityl chloride; at 30 ℃; for 6h; Large scale;

4-biphenyl-carboxylic acid chloride; at 30 ℃; for 2h; Temperature; Large scale;

Reference yield: 91.0%

<3aS(2aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)-4-(butyryloxymethyl)hexahydro-2H-cyclopentafuran-2-one (127783-76-0) → <3aS(3aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one (39265-57-1)

Guidance literature:

With Amberlite IR-120; In methanol; for 20h; Heating;

DOI:10.1135/cccc19920357

Reference yield: 78.0%

<3aS(3aα,4α,5β,6aα)>-(+)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate (136982-10-0) → <3aS(3aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one (39265-57-1)

Guidance literature:

With sulfuric acid; In methanol; for 15h; Heating;

upstream raw materials:

<3aS(3aα,4α,5β,6aα)>-(+)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen butanedioate

<3aS(3aα,4α,5β,6aα)>-(+)-<5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-2H-cyclopentafuran-2-on-4-yl>methyl hydrogen pentanedioate

<3aS(2aα,4α,5β,6aα)>-(+)-5-(1,1'-biphenyl-4-carbonyloxy)-4-(butyryloxymethyl)hexahydro-2H-cyclopentafuran-2-one

<3aR(3aα,4α,5β,6aα)>-(-)-5-(1,1'-biphenyl-4-carbonyloxy)hexahydro-4-hydroxymethyl-2H-cyclopentafuran-2-one

Downstream raw materials:

(Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

(3aS,4R,5S,6aR)-hexahydro-5-(biphenyl-4-formyloxy)-4-(tert-butyldimethylsilyloxy methyl)-2H-cyclopenta[b]furan-2-one