100757-47-9

Upstream product

• 84230-96-6 (2S,3S)-3-<(tertbutyl)dimethylsilyloxy>-2-methylpentan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 100235-81-2 methyl (2R,3R)-2-methyl-3-tetrahydropyranyloxypentenoate 
• 86535-09-3 (2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentanol 
• 78433-57-5 (2S,3R)-2-methylpentane-1,3-diol 1-benzyl ether 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 100699-14-7 (2S,3S)-3-t-butyldimethylsilyloxy-2-methylpentane-1-ol 1-benzyl ether 
• 86535-08-2 (2S,3R)-2-methylpentane-1,3-diol 1-benzyl,3-THP-ether 
• 149-31-5 (2S,3S)-2-methylpentane-1,3-diol 
• 77302-11-5 [2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 86535-14-0 (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 
• 124356-91-8 (4R)-3-[(2R,3S)-3-hydroxy-2-methyl-pentanoyl]-4-benzyl-oxazolidine-2-one 

Downstream Products

• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 

Relevant academic research and scientific papers

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%.

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.