86535-14-0

Basic information

• Product Name: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol
• Synonyms: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol
• CAS NO: 86535-14-0
• Molecular Weight: 272.365
• Mol File: 86535-14-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol(86535-14-0)
• EPA Substance Registry System: (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol(86535-14-0)

Safety Data

• Hazardous Substances Data: 86535-14-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 86535-06-0 (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate 
• 86562-30-3 (2R,3R)-dimethyl threo-3-methylmalate THP ether 
• 86535-08-2 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 13398-40-8 (2R,3R)-threo-β-methylmalic acid 
• 86562-31-4 (2R,3S)-threo-3-methylbutane-1,2,4-triol 2-THP ether 
• 86535-09-3 (2S,3S)-3-Tetrahydropyranyloxy-2-methylpentan-1-ol 
• 71565-21-4 (2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol 
• 77333-26-7 (2R,3S)-threo-3-methylbutane-1,2,4-triol 
• 86562-32-5 (2R,3S)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 4-benzyl ether 
• 81380-12-3 (2S,3R)-3,4-epoxy-2-methyl-1-butanol benzyl ether 
• 77398-86-8 dimethyl (2R,3R)-2-hydroxy-3-methylsuccinate 
• 81422-90-4 (2R,3S)-threo-3-methylbutane-1,2,4-triol 4-benzyl ether 

Downstream Products

• 86535-18-4 2-methyl-3-pentanol (S)-(-)-MTPA ester 
• 86535-19-5 2-methyl-3-pentanol (R)-(+)-MTPA ester 
• 155393-14-9 (2S,3S)-3-O-acetyl-2-methyl-1-O-p-toluenesulfonyl-1,3-pentanediol 
• 100757-47-9 (2S,3S)-3-t-butyldimethylsilyloxy-2-methyl-1-(4-methylbenzenesulfonyloxy)pentane 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 

Relevant articles and documents

A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin

(4RS,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone (serricornin and its C4- epimer) may be prepared from oxazolidinone 5 in 8 steps with an overall yield of 33%.

CHIRALITY TRANSFER IN THE ESTER ENOLATE CLAISEN REARRANGEMENT OF (R)-1-METHYL-(E)-2-BUTENYL HYDROXYACETATE AND ITS APPLICATION TO THE STEREOCONTROLLED PHEROMONE SYNTHESIS

The ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2- butenyl hydroxaacetate provides complete asymmetric transfer along with 98percent erythroselectivity to give (2R,3S)-2-hydroxy-3-methyl-(E)-4-hexenoic acid.Its synthetic utility is demonstrated by the stereocontrolled synthesis of optically active pheromones.