196703-73-8

Upstream product

• 71338-71-1 benzyl (E)-2-butenoate 
• 71338-71-1 benzyl crotonate 
• 100-51-6 benzyl alcohol 

Relevant academic research and scientific papers

Scalable synthesis of enantiomerically pure syn -2,3-dihydroxybutyrate by sharpless asymmetric dihydroxylation of p -phenylbenzyl crotonate

An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.

Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer

The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from d-mannitol via (2R)-2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescence-inducing properties in the Vibrio harveyi BB170 strain.

Asymmetric dihydroxylation onto the α,β-unsaturated carboxylic ester derivatives of camptothecin

Dihydroxyalkanoic ester derivatives (4a,b) and (5a,b) of 20S-camptothecin (1) were diastereoselectively synthesized by exploiting osmium-catalyzed asymmetric dihydroxylation based on the Sharpless procedure. The absolute configuration of the newly formed