67253-77-4

Upstream product

• 67253-83-2 erythro-(2S,3S,7S)-3,7-dimethylpentadecan-2-ol 
• 79-03-8 propionyl chloride 
• 123-62-6 propionic acid anhydride 
• 120664-05-3 threo-(2R,3S,7S)-3,7-dimethylpentadecan-2-ol 
• 802294-64-0 propionic acid 
• 84567-97-5 (S)-1-Bromo-3-methylundecane 
• 67214-66-8 (4S)-4-methyl-1-dodecyl bromide 
• 67214-63-5 (S)-2,6-dimethyltetradec-2-ene 
• 67214-64-6 (4S)-4-methyl-1-dodecanol 
• 1413919-16-0 (2S,6S)-2,6-dimethyltetradecanal 
• 111-25-1 1-bromo-hexane 
• 107650-07-7 (3S)-4,4-dimethoxy-3-methylbutan-1-ol 
• 1283688-51-6 methyl (3S)-4,4,4-trimethoxy-3-methylbutanoate 
• 1413919-17-1 (2S,3S,7S)-3,7-dimethylpentadec-2-yl-3,5-dinitrobenzoate 

Relevant academic research and scientific papers

Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate and propionate, the sex pheromones of pine sawflies

The stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate (2) and propionate (3) was accomplished by utilizing the cheap and easily available chiron (R)-4-methyl-δ-valerolactone (4). The key steps were chelation-controlled addition of Gilmann reagent to chiral β-alkoxy aldehyde 12 and the Cu(I)-catalyzed coupling of Grignard reagent with bromoester 5 in the presence of NMP.

Asymmetric syntheses of the sex pheromones of pine sawflies, their homologs and stereoisomers

We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis, their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e., 126. A total of 48 compounds, including acetates 78-101 and propanoates 102-125, have been synthesized. Our general approach towards these compounds originated from the commercially available chirons diethyl (S)- and (R)-malates, as well as ethyl (R)-3-hydroxybutanoate. The Seebach asymmetric methylation was employed in a key step to control additional configuration. Copyright

Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol and its propionate, the sex pheromones of pine sawflies

The stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (diprionol) and its propionate, the sex pheromones of pine sawflies (Neodiprion sp. and other), in high enantiomeric purity was achieved from (1R,3S)-2,2-dichloro-3-methylcyclopropane

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.

CHIRAL SYNTHESIS OF (2S,3S,7S)-3,7-DIMETHYLPENTADECAN-2-YL ACETATE AND PROPIONATE, POTENTIAL SEX PHEROMONE COMPONENTS OF THE PINE SAW-FLY NEODIPRION SERTIFER (GEOFF.)

A synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and propionate (3) is described. (2S)-2-Methyldecan-1-yl lithium (5) was reacted with (3S,4S)-3,4-dimethyl-γ-butyrolactone (6) to yield the ketoalcohol 19 which upon Huang-Minlon reduction furnished (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (1).Acylations gave the esters 2 and 3.The (2S)-2-methyldecan-1-yl lithium was obtained via asymmetric synthesis.The chiral lactone 6 was obtained from (2S,3S)-trans-2,3-epoxybutane and dimethylmalonate.