138761-04-3

Upstream product

• 138760-89-1 (Z)-(S)-2-(Acetoxymethyl)hept-3-en-1-ol 
• 138760-93-7 (Z)-(R)-2-Triisopropylsilanyloxymethyl-hept-3-en-1-ol 
• 138436-27-8 (R)-(E)-2-<<<(-p-Methoxybenzyl)oxy>methoxy>methyl>-1-<(triisopropylsilyl)oxy>-5-methylhex-3-ene 
• 138436-32-5 (R)-2-(4-Methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-propionaldehyde 

Downstream Products

• 159992-97-9 (2R,3S)-2-[(S)-1-Benzyloxymethoxymethyl-2-(4-methoxy-benzyloxymethoxy)-ethyl]-3-propyl-oxirane 

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.