138760-95-9

Upstream product

• 155125-04-5 (S)-1-(4-methoxybenzyloxymethoxy)-2-(triisopropylsilyloxymethyl)-3(Z)-heptene 
• 138760-89-1 (Z)-(S)-2-(Acetoxymethyl)hept-3-en-1-ol 
• 138436-27-8 Triisopropyl-[(E)-(S)-2-(4-methoxy-benzyloxymethoxymethyl)-5-methyl-hex-3-enyloxy]-silane 
• 138436-32-5 (S)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde 
• 138436-19-8 (R)-(E)-2-<<<(p-Methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-en-1-ol 
• 88023-78-3 para-methoxybenzyl chloride 

Downstream Products

• 155125-20-5 (S)-3-Benzyloxymethoxy-2-((2S,3R)-3-propyl-oxiranyl)-propan-1-ol 
• 155125-21-6 [(R)-3-Benzyloxymethoxy-2-((2S,3R)-3-propyl-oxiranyl)-propoxy]-triisopropyl-silane 
• 155125-19-2 (2S,3R)-2-[(R)-1-Benzyloxymethoxymethyl-2-(4-methoxy-benzyloxymethoxy)-ethyl]-3-propyl-oxirane 
• 155125-14-7 (R)-2-(4-methoxybenzyloxymethoxy)-3(Z)-hepten-1-ol 

Relevant academic research and scientific papers

Stereodivergent synthesis of cis epoxides derived from asymmetrized 2-alkenyl-1,3-propanediols

Cis epoxides of any desired absolute stereochemistry have been obtained in a high enantio- and diastereodivergent manner via diastereospecific epoxidation of asymmetrized (Z)-2-alkenyl-1,3-propanediols, in turn obtained through a chemoenzymatic route, and a protection-deprotection 'trick' on hydroxy groups.

Stereoselective epoxidation of asymmetrized 2-alkenyl-1,3-propanediols

Asymmetrized 2-alkenyl 1,3-propanediols are stereoselectively epoxidized to the same main diastereoisomer both with 3-chloroperbenzoic acid and the VO(acac)2/t-butyl hydroperoxyde system. Using the latter epoxidating reagent in combination with a protection-deprotection sequence involving the two homoallylic hydroxy groups, all the four cis epoxides were easily achieved in stereoisomeric pure from starting from a single common (Z) precursor.