86535-08-2

Upstream product

• 100-44-7 benzyl chloride 
• 86535-09-3 (2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentanol 
• 86562-29-0 (2R,3R)-(-)-threo-3-methylaspartic acid 
• 642-92-2 D,L-threo-β-methylaspartic acid 
• 86535-06-0 (2R,3S)-threo-3-methylbutane-1,2,3-triol 4-benzyl ether 1-tosylate 
• 13398-40-8 (2R,3R)-threo-β-methylmalic acid 
• 86562-31-4 (2R,3S)-threo-3-methylbutane-1,2,4-triol 2-THP ether 
• 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 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 78433-57-5 (2S,3R)-2-methylpentane-1,3-diol 1-benzyl ether 
• 149-31-5 (2S,3S)-2-methylpentane-1,3-diol 
• 86535-09-3 (2S,3S)-3-Tetrahydropyranyloxy-2-methylpentan-1-ol 
• 72598-35-7 (-)-serricornin 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 
• 82335-98-6 serricornin acetate <(4S,6R,7R)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 86535-14-0 (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 
• 86535-19-5 2-methyl-3-pentanol (R)-(+)-MTPA ester 
• 86535-18-4 2-methyl-3-pentanol (S)-(-)-MTPA ester 
• 86535-10-6 (2S,3S)-threo-2-methylpentane-1,3-diol 3-THP ether 1-tosylate 
• 100762-79-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-3-benzyloxy-1-ethyl-2-methyl-propyl ester 
• 100699-13-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-3-benzyloxy-1-ethyl-2-methyl-propyl ester 

Relevant academic research and scientific papers

A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle

Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.

SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN

The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by