173092-00-7

Basic information

• Product Name: (S)-2-benzyl-5-methyl-hex-4-en-1-ol
• Synonyms: (S)-2-benzyl-5-methyl-hex-4-en-1-ol
• CAS NO: 173092-00-7
• Molecular Weight: 204.312
• Mol File: 173092-00-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-2-benzyl-5-methyl-hex-4-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-benzyl-5-methyl-hex-4-en-1-ol(173092-00-7)
• EPA Substance Registry System: (S)-2-benzyl-5-methyl-hex-4-en-1-ol(173092-00-7)

Safety Data

• Hazardous Substances Data: 173092-00-7(Hazardous Substances Data)

Upstream product

• 178032-88-7 (S)-4-Benzyl-3-((S)-2-benzyl-5-methyl-hex-4-enoyl)-oxazolidin-2-one 
• 645-45-4 hydrocinnamic acid chloride 
• 136159-65-4 (S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one 
• 870-63-3 prenyl bromide 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 320606-25-5 (S)-2-benzyl-5-methyl-hex-4-enal 

Downstream Products

• 173091-89-9 C₆₀H₇₉N₃O₁₀Si 
• 173092-02-9 (2S,5'S)-5'-Benzyl-5'-((4S,5S)-4-benzyl-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-5-ylmethyl)-4-((R)-1-carboxy-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-[2,3']bipyrrolyl-1,1'-dicarboxylic acid diallyl ester 
• 173092-09-6 (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 173091-97-9 {(1S,2S)-1-Benzyl-3-[(2S,5'S)-5'-benzyl-4-((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-yl]-2-hydroxy-propyl}-carbamic acid (S)-(tetrahydro-furan-3-yl) ester 
• 173091-91-3 (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 173091-90-2 (4S,5S)-4-Benzyl-5-[(2S,5'S)-5'-benzyl-4-((R)-1-carboxy-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 173091-94-6 (R)-2-((2S,5'S)-5'-Benzyl-5'-{(2S,3S)-2-hydroxy-4-phenyl-3-[(S)-(tetrahydro-furan-3-yl)oxycarbonylamino]-butyl}-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl)-3-phenyl-propionic acid methyl ester 
• 173240-66-9 {(1S,2S)-1-Benzyl-3-[(2S,5'S)-5'-benzyl-4-((R)-1-carbamoyl-2-phenyl-ethyl)-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-yl]-2-hydroxy-propyl}-carbamic acid (S)-(tetrahydro-furan-3-yl) ester 
• 173091-95-7 (R)-2-[(2S,5'S)-5'-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-5'-benzyl-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-N-tert-butyl-3-phenyl-propionamide 
• 173091-92-4 (R)-2-[(2S,5'S)-5'-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-5'-benzyl-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionamide 
• 173091-98-0 (R)-2-[(2S,5'S)-5'-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-5'-benzyl-2-isobutyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester 
• 173092-01-8 (S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-2-(3-methyl-but-2-enyl)-3-oxo-2,3-dihydro-pyrrole-1-carboxylic acid allyl ester 
• 173091-86-6 {(S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-2-isobutyl-3-oxo-2,3-dihydro-1H-pyrrol-2-yl}-acetaldehyde 
• 173091-87-7 (R)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-butyraldehyde 

Relevant articles and documents

SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes

The proclivity of α-branched N-2′-benzyl-3′-phenylpropionyl derivatives of (S)-4-benzyl-5,5-dimethyl-, (S)-4-phenyl-5,5-dimethyl-, (S)-4-isopropyl-5,5-dimethyl-, (S)-4-benzyl- and (S)-4-benzyl-5,5-diphenyl-oxazolidin-2-ones to generate directly 2-benzyl-3-phenylpropionaldehyde upon hydride reduction with DIBAL is investigated. The (S)-4-benzyl-5,5-dimethyl-derivative proved optimal for inhibition of endocyclic nucleophilic attack, giving 2-benzyl-3-phenylpropionaldehyde in good yield upon reduction. Application of this methodology for the asymmetric synthesis of chiral aldehydes via diastereoselective enolate alkylation of a range of (S)-N-acyl-4-benzyl-5,5-dimethyloxazolidin-2-ones to afford an array of α-substituted-N-acyl-5,5-dimethyloxazolidin-2-ones (85-94% de) and subsequent reduction with DIBAL afforded directly non-racemic α-substituted aldehydes without loss of stereochemical integrity (87-94% ee). The extension of this protocol for the asymmetric synthesis of β-substituted aldehydes is demonstrated, via the diastereoselective conjugate addition of a range of organocuprates to (S)-N-acyl-4-phenyl-5,5-dimethyloxazolidin-2-ones which proceeds with high diastereoselectivity (generally >95% de). Reduction of the conjugate addition products with DIBAL gives non-racemic β-substituted aldehydes in high yields and in high ee (generally >95% ee). This methodology is exemplified by the asymmetric synthesis of (R)-3-isopropenylhept-6-enal, which has previously been used in the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromones of the California red scale.

Pyrrolinone-based HIV protease inhibitors. Design, synthesis, and antiviral activity: Evidence for improved transport

Pyrrolinone-based peptidomimetics, the first mimics of β-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived