(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate
• CAS No.: 39746-00-4
• Molecular Formula: C15H16O5
• Molecular Weight: 276.289
• Hs Code.: 29321900
• European Community (EC) Number: 254-615-6
• DSSTox Substance ID: DTXSID90960341
• Nikkaji Number: J28.204I
• Wikidata: Q72461471
• Mol file: 39746-00-4.mol

Synonyms:39746-00-4;(-)-Corey lactone benzoate;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate;Corey lactone benzoate;(3aR,4S,5R,6aS)-(-)-5-(benzoyloxy)-hexahydro-4(-hydroxymethyl)-2H-cyclopenta[b]furan-2-one;[(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate;(3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one;(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one;(3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopentafuran-2-one;SCHEMBL2973096;DTXSID90960341;MFCD00674102;AKOS024462902;AC-6091;AS-16023;C2605;CS-0003842;(1S,5R,6S,7R)-6-hydroxymethyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one;(3aR,4S, 5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate;(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-ylbenzoate;2H-Cyclopenta[b]furan-2-one,5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-, (3aR,4S,5R,6aS)-

Chemical Property of (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Chemical Property:

• Appearance/Colour: Colorless crystalline powder
• Vapor Pressure: 4.24E-10mmHg at 25°C
• Melting Point: 116-120 °C
• Refractive Index: 1.587
• Boiling Point: 481.9oC at 760 mmHg
• PKA: 14.79±0.10(Predicted)
• Flash Point: 183.3oC
• PSA: 72.83000
• Density: 1.33g/cm3
• LogP: 1.15590
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 276.09977361
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

99%min ^*data from raw suppliers

(-)-Corey Lactone Benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=CC=C3)CO
• Isomeric SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)CO
• Uses: (-)-Corey Lactone Benzoate is a corey lactone derivative used in the preparation prostaglandin analogues for use as vasolidator as well as EP4 receptor agonists.

Technology Process of (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

There total 12 articles about (3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-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: 100.0%

Benzoic acid (3aR,4S,5R,6aS)-2-oxo-4-triethylsilanyloxymethyl-hexahydro-cyclopenta[b]furan-5-yl ester → (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In dichloromethane; at 20 ℃; for 0.0333333h; atmospheric pressure;

DOI:10.1016/j.tetlet.2003.12.145

Reference yield: 99.0%

(1S,5R,6S,7R)-6-tert-Butyldimethylsilyloxymethyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one → (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In dichloromethane; at 20 ℃; for 4h; atmospheric pressure;

DOI:10.1016/j.tetlet.2003.12.145

Reference yield: 69.0%

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at 0 ℃; for 0.416667h;

upstream raw materials:

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

(3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one

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

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

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

(3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydrocyclopenta(b)furan-2-one

(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one

dinoprost

Refernces

• 1、 -. "Preparing method for benzoyl corey lactone". Paragraph 0099-0107. . Retrieved 2019/01/15.
• 2、 T?nase, Constantin I.,Dr?ghici, Constantin. "Transformation of δ-lactone in γ-lactone in the Corey route for synthesis of prostaglandins". . p. 845 - 853. Retrieved 2015/06/30.