99902-69-9

Upstream product

• 922-65-6 divinylcarbinol 
• 99902-68-8 (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 121405-00-3 (+/-)-2,3-Epoxy-1-tosyloxypent-4-ene 
• 78260-12-5 (+/-)-2,3-Epoxypent-4-en-1-ol 
• 121405-04-7 (+/-)-4-Tosyloxymethyl-5-vinyl-1,3-dioxolan-2-one 
• 121521-25-3 (-)-(2S,3S)-2,3-epoxypent-4-en-1-ol 
• 100017-22-9 (S)-1-[(R)-oxiran-2-yl]prop-2-enol 
• 100017-24-1 (2R,3S)-pent-4-ene-1,2,3-triol 
• 98-59-9 p-toluenesulfonyl chloride 
• 212579-64-1 (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 
• 287934-61-6 (2R)-4-pentene-1,2,3-triol 

Downstream Products

• 121469-49-6 [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate 
• 100017-25-2 (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane 
• 133814-94-5 (2S,3R)-2,3-O-isopropylidene-1-O-p-tosyl-4-pentene-1,2,3-triol 
• 100017-25-2 Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-ylmethyl ester 
• 121405-02-5 (+/-)-(2S,4R,5S)-2-Methyl-2-<2-(phenylsulfonyl)ethyl>-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 121405-03-6 (+/-)-(1R,5S,7S)-5-Methyl-3-phenylsulfonyl-7-vinyl-6,8-dioxabicyclo<3.2.1>octane 
• 99902-68-8 (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 121405-06-9 (+/-)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane 

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.

Synthesis of Side-Chain Unsaturated endo- and exo-Brevicomins. Representatives of Pheromone Analogs in the Dioxabicyclooctane Series

The title substances endo- and exo-9 were synthesized via selective trans- and cis-opening of the epoxy tosylate 3, respectively.The tosylate 3 is easily obtainable from pentadienol 1.