38754-71-1

Basic information

• Product Name: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester
• Synonyms: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester;(-)-Corey Lactone aldehyde P-Phenyl Benzoate;(3aR,4R,5R,6aS)-4-ForMyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate;Corey Lactone Aldehyde phenylbenzoate
• CAS NO: 38754-71-1
• Molecular Formula: C₂₁H₁₈O₅
• Molecular Weight: 350.36
• Mol File: 38754-71-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 574.827 °C at 760 mmHg
• Flash Point: 253.713 °C
• Appearance: /
• Density: 1.32
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Solubility: DCM, Ethyl Acetate
• CAS DataBase Reference: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester(38754-71-1)
• EPA Substance Registry System: [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester(38754-71-1)

Safety Data

• Hazardous Substances Data: 38754-71-1(Hazardous Substances Data)

Usage

Uses

(3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1''-biphenyl]-4-carboxylate is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.

InChI:InChI=1/C21H18O5/c22-12-17-16-10-20(23)25-18(16)11-19(17)26-21(24)15-8-6-14(7-9-15)13-4-2-1-3-5-13/h1-9,12,16-19H,10-11H2/t16-,17-,18+,19-/m1/s1

Upstream product

• 139108-43-3 (3aR,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-4-vinyl-hexahydro-cyclopenta[b]furan-2-one 
• 139108-44-4 (3aR,6aS)-4-Vinyl-tetrahydro-cyclopenta[b]furan-2,5-dione 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 139108-47-7 Biphenyl-4-carboxylic acid (3aR,5R,6aS)-2-oxo-4-vinyl-hexahydro-cyclopenta[b]furan-5-yl ester 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 

Downstream Products

• 31753-00-1 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 69868-34-4 4-Biphenylcarbonsaeure-<6-<(3-cyanpropyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 69868-20-8 4-Biphenylcarbonsaeure-<6-<(4-tert-butyloxycarbonylbutyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 73102-78-0 4-Biphenylcarbonsaeure-<6-<(4-methylthiomethylphenyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo-<3.3.0>octylester> 
• 71158-75-3 4-Biphenylcarbonsaeure-<6-<(bicyclo<2.2.1>hept-2-en-5-yl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>-octylester> 
• 69868-24-2 4-Biphenylcarbonsaeure-<6-<(4-tert-butyloxycarbonyl-1-methylbutyl)-carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 69868-42-4 4-Biphenylcarbonsaeure-<6-<(2-piperidinocarbonylethyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 81266-76-4 4-Biphenylcarbonsaeure-<6-<(3-cyan-1-benzylpropyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>-octylester> 
• 69868-39-9 4-Biphenylcarbonsaeure-<6-<(6-piperidinocarbonylhexyl)carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 81266-75-3 4-Biphenylcarbonsaeure-<6-<<4-(1-m-chlorphenyl-1-methylethoxy)carbonylbutyl>carbonylvinyl>-3-oxo-2-oxa-7-bicyclo<3.3.0>octylester> 
• 79171-99-6 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-5-yl ester 
• 61188-88-3 4β-<8-Methoxy-4(RS)-methyl-3-oxo-1-(trans)octenyl>-2-oxo-5α-p-phenylbenzoyloxy-3,3aβ,4α,5β,6,6aβ-hexahydro-2H-cyclopentafuran 
• 79171-94-1 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-[(E)-4-(4-chloro-phenoxy)-3-oxo-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 54324-79-7 (3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate 

Relevant articles and documents

A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.

Preparation method for prostaglandins drug intermediate

The invention discloses a preparation method for (3aR,4R,5R,6aR)-4-aldehyde-hexahydro-2-oxo-2H-cyclopentano[b]furan-5-yl[1,1'-biphenyl]-4-foremate, and belongs to the technical field of the medical intermediate preparation. Compared with a former Pfitzner

An improved and efficient process for the preparation of (+)-cloprostenol

Abstract An improved and efficient synthesis of (+)-cloprostenol has been accomplished in nine steps and 26% overall yield from commercially available (-)-Corey lactone 4-phenylbenzoate alcohol 1. The present route avoids tedious purifications and require