177213-31-9

Upstream product

• 177213-30-8 (E)-1-p-toluenesulfonyl-2-iodoheptene 
• 82721-81-1 1-(p-toluenesulfonyl)-1-heptyne 
• 628-71-7 1-Heptyne 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 1035797-60-4 2-pentyl-3-(toluene-4-sulfonyl)-oxirane 
• 128707-15-3 (2R,4S,5S)-tetrahydro-4-hydroxy-5-pentyl-2-furfuraldehyde (benzoate) 
• 221187-58-2 (2S,5R)-5-Benzyloxymethyl-2-pentyl-dihydro-furan-3-one 
• 221187-63-9 (2S,3R,5R)-5-Benzyloxymethyl-2-pentyl-tetrahydro-furan-3-ol 
• 951133-94-1 (+)-(2S,3S,5R)-3-phenylcarbonyloxy-5-hydroxymethyl-2-pentyl-tetrahydrofuran 

Relevant academic research and scientific papers

Synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala, by an oxiranyl anion strategy

The stereocontrolled synthesis of (6S,7S,9R,10R)-6,9-epoxynonadec-18- ene-7,10-diol, isolated from the brown alga, Notheia anomala, has been achieved. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by alkylation of the sulfonyl-stabilized oxiranly anion followed by 5-endo cyclization.

Alkylation of oxiranyl anions

Oxiranyllithium compounds generated from epoxy sulfones by deprotonation with n-butyllithium in THF at -100°C react with α-alkoxy alkyl triflates to give new substituted epoxides in high yields.