156767-45-2

Basic information

• Product Name: (2R)-2-methyl-5-phenylpentan-1-al
• Synonyms: (2R)-2-methyl-5-phenylpentan-1-al
• CAS NO: 156767-45-2
• Molecular Weight: 176.258
• Mol File: 156767-45-2.mol

Chemical Properties

• CAS DataBase Reference: (2R)-2-methyl-5-phenylpentan-1-al(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-methyl-5-phenylpentan-1-al(156767-45-2)
• EPA Substance Registry System: (2R)-2-methyl-5-phenylpentan-1-al(156767-45-2)

Safety Data

• Hazardous Substances Data: 156767-45-2(Hazardous Substances Data)

Upstream product

• 2857-75-2 (R)-4-methyl-δ-valerolactone 
• 108-86-1 bromobenzene 
• 156661-58-4 (+)-3-(5-Phenyl-2(R)-methyl-1-oxopentyl)-4(S)-isopropyl-1,3-oxazolidin-2-one 
• 4392-24-9 Cinnamyl bromide 
• 104554-86-1 (+)-3-(5-Phenyl-2(R)-methyl-1-oxo-4(E)-pentenyl)-4(S)-isopropyl-1,3-oxazolidin-2-one 
• 75-24-1 trimethylaluminum 
• 156767-44-1 (+)-(R)-2-Methyl-5-phenyl-1-pentanol 

Downstream Products

• 156661-61-9 (-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester 
• 171190-05-9 tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,6(4E,6R),7R]-1-(4-acetoxy-5-methyl-6-phenylhexyl)-7-(tert-butoxycarbonyloxy)-4-hydroxy-6-(6-methyl-9-phenyl-4-nonenoyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 
• 146389-62-0 (+)-zaragozic acid 
• 156661-57-3 (R)-9-phenyl-6-methyl-4-nonenoic acid 

Relevant articles and documents

Diastereoselective protonation of dienols: A formal approach to zaragozic acid C side chain

The 2-methyl 5-phenylpropanal precursor of the side chain of zaragozic acid C has been prepared in 83% ee through the diastereoselective protonation of a photodienol generated in situ by irradiation of an α,β-unsaturated ester, bearing, as a chiral moiety

"One-pot" reductive lactone alkylation provides a concise asymmetric synthesis of chiral isoprenoid targets

An efficient method, based on nucleophilic addition to lactones followed by modified in situ Clemmensen reduction, provides a short synthetic route to chiral isoprenoid targets. The efficacy of this method has been exemplified through the synthesis of several targets including the commercial fragrance Rosaphen, the side chain of Zaragozic acid C, the cotton leaf sex pheromone, and the side chains of vitamin E.

(+)-Zaragozic acid C: Synthesis and related studies

The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)2·H2O]2 for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of γ-alkoxy-α,β-trans enones, and (3) nucleophilic addition of Me3SiC≡CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.