144895-64-7

Upstream product

• 848566-19-8 (E,4S,5S)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 
• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 90661-39-5 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 

Downstream Products

• 144895-70-5 (E)-(2S,5R)-6-Benzyloxy-2-butyl-5-hydroxy-hex-3-enoic acid ethyl ester 
• 144895-69-2 (3E,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate 
• 144895-68-1 (E)-(2S,5R)-6-Benzyloxy-5-hydroxy-2-methyl-hex-3-enoic acid ethyl ester 

Relevant academic research and scientific papers

Addition of Organocopper Reagents to Cyclic Sulfites or Carbonates of γ,δ-Dihydroxy (E)-α,β-Enoates

Reaction of cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R=Me-, n-Bu-) afforded either diastereoselective SN2' products or reductive elimination product depending on reaction conditions.Addition of R2Cu(CN)Li2, BF3 (R=Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectivity α-alkylation products (6 and 8).By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.