145050-11-9

Upstream product

• 136258-90-7 cis-2,3-epoxybutane-1,4-diacetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 136258-94-1 (2R,3S)-4-Acetoxy-4-tert-butyldiphenylsilyloxy-2,3-epoxybutane 
• 136258-92-9 (2S,3R)-4-Acetoxy-2,3-epoxybutan-1-ol 

Downstream Products

• 145050-12-0 (2R,3S)-4-tert-Butyldiphenylsilyloxy-2,3-epoxybutyl tosylate 
• 145050-14-2 (2S,3R)-1-tert-Butyldiphenylsilyloxy-2,3-epoxytetradecane 
• 145050-13-1 (2S,3R)-1-tert-Butyldiphenylsilyloxy-2,3-epoxy-8-methylnonane 
• 131484-41-8 erythro-(2R,3S)-4-(tert-butyldimethylsiloxy)-2,3-epoxy-1-butanol 

Relevant academic research and scientific papers

Pheromone synthesis; CXXXIX. Enzymatic preparation of (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol and its conversion to the epoxy pheromones of the gypsy moth and the ruby tiger moth

Pig pancreatic lipase-catalyzed asymmetric hydrolysis of 1,4-diacetoxy-cis-2,3-epoxybutane yielded (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol, which was converted to two naturally occurring epoxides: the gypsy moth pheromone, disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] and the ruby tiger moth pheromone [(6Z,9S,10R)-9,10-epoxy-6-henicosene].

APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS

Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.