136459-46-6

Upstream product

• 113826-06-5 (R)-glycidyl tosylate 
• 70987-78-9 (S)-Glycidyl tosylate 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 445030-22-8 (S)-4-tosyloxymethyl-1,3,2-dioxathiolane-2,2-dioxide 
• 136404-79-0 (R)-1-azido-2-trimethylsilyloxy-3-tosyloxypropane 
• 98-59-9 p-toluenesulfonyl chloride 
• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 

Downstream Products

• 285562-01-8 (S)-α-(azidomethyl)-4-[2-(1-methylethoxy)phenyl]-1-piperazineethanol 

Relevant academic research and scientific papers

Nucleophilic reaction of glycidol tosylate and the corresponding cyclic sulfate with various nucleophiles: A comparative study

The nucleophilic reaction of glycidol tosylate and the corresponding cyclic sulfate tosylate have been carried out with a number of nucleophiles to study the possible attack of nucleophiles at C1, C2 or C3 positions. The regioselectivity and reactivity of both the substrates i.e. epoxide tosylate 1 and the corresponding cyclic sulfate 2 have been compared and established that under similar conditions cyclic sulfate counterpart shows better regioselectivity and better reactivity than the corresponding epoxide.

Ring-opening of glycidyl derivatives by silanes mediated by Ti(O-i-Pr)4 or Al(O-i-Pr)3: Access to versatile C3 building blocks

Ring-opening of chiral glycidol or glycidyl tosylate by Me3SiN3 or Me3SiCN catalyzed by Ti(O-i-Pr)4 or Al(O-i-Pr)3 occurred in a regiospecific manner and with very high stereoselectivity, leading to new trifunctionalized chiral building blocks. The enantiomeric excess of the ring-opened products was 90-95%, as determined by 1H NMR of the Mosher ester derivatives, indicating that there was no significant loss of optical purity during the ring-opening. This methodology was applied for the one-pot synthesis of (R)-1-azido-3-naphthyloxy-2-hydroxypropane in 94% ee, a precursor of analogs of propranolol.