848644-70-2

Upstream product

• 709027-84-9 diethyl (2S,3R)-3-methyl-O-(p-toluenesulfonyloxy)malate 
• 116782-41-3 (2S,3S)-2-methylbutane-1,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 92935-19-8 (2S,3S)-2-methyl-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butyl 4-methylbenzenesulfonate 
• 67253-77-4 (2S,3S,7S)-3,7-dimethylpentadecan-2-yl propionate 

Relevant academic research and scientific papers

A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate and propionate, the sex pheromones of pine sawflies

(2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction-epoxide formation-reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.