565183-89-3

Upstream product

• 24529-80-4 (E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol 
• 43160-61-8 (E)-3,6-dimethyl-2,5-heptadien-1-ol 
• 565183-74-6 (2R,3R)-2,3-epoxy-3,6-dimethyl-5-hepten-1-ol 
• 53170-97-1 (E)-4-chloro-3-methyl-2-buten-1-ol 
• 565183-88-2 (2R,3R)-1-O-tert-butyldiphenylsilyl-2,3-epoxy-3,6-dimethyl-5-hepten-1-ol 

Downstream Products

• 565183-92-8 tert-Butyl-{(2R,3R)-3-methyl-3-[(2R,3R)-3-methyl-3-(3-methyl-but-2-enyl)-oxiranylmethyl]-oxiranylmethoxy}-diphenyl-silane 
• 565183-91-7 (2R,3R,5R,6R)-7-bromo-1-O-tert-butyldiphenylsilyl-2,3;5,6-diepoxy-3,6-dimethylheptan-1-ol 
• 565183-90-6 {(2R,3R)-3-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranylmethyl]-2-methyl-oxiranyl}-methanol 

Relevant academic research and scientific papers

Biomimetic synthesis of fused polypyrans: Oxacyclization stereo- and regioselectivity is a function of the nucleophile

(Matrix presented) The stereoselectivity of Lewis acid-induced endo-regioselective oxacyclizations of 1,4-diepoxides is dependent upon the nature of the terminating nucleophile. For instance, the tert-butyl carbonate-substituted diepoxide of 3,6-dimethylhepta-2,5-dien-1-ol provides a cis-fused bicyclic product, whereas the N,N-dimethylcarbamate derivative affords the trans-fused diastereomer. Stereospecific and regioselective conversion of the tertiary carbamate-terminated 1,4,7-triepoxide (I) to tricyclic all-trans-fused polypyran (II) is also demonstrated.