133782-91-9

Upstream product

• 133782-90-8 (2R,4S,5R)-5-hydroxy-2-phenyl-4-vinyl-1,3-dioxane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 100017-22-9 (S)-1-[(R)-oxiran-2-yl]prop-2-enol 
• 121521-25-3 (-)-(2S,3S)-2,3-epoxypent-4-en-1-ol 
• 100017-24-1 (2R,3S)-pent-4-ene-1,2,3-triol 

Relevant academic research and scientific papers

ASYMMETRIC SHARPLESS EPOXIDATION OF DIVINYLCARBINOL. erythro-D- AND -L-4-PENTENITOLS BY HYDROLYSIS OF REGIOISOMERIC EPOXY-4-PENTENOLS

The asymmetric Sharpless epoxidation of divinylcarbinol (1), a secondary, achiral allylic alcohol, is described in detail.The epoxidation proceeds with high enantio-control and diastereo-selection.The resulting 1,2-epoxy-4-pentene-3-ols 2 are equilibrated to afford the internal epoxides 5.Hydrolysis of the regioisomers 2 and 5, respectively, furnishes opposite enantiomers of erythro-4-pentenitols 3 with high selectivity.Several derivatives of 3 are described, as well as result of a less stereoselective route - from D-glyceraldehyde acetonide (10) - providing NMR data of the threo series. - The acute toxicity of divinylcarbinol (1) is reported, along with the mutagenicity of 1, L-2 and L-5 as determined by Ames tests.