848566-36-9

Upstream product

• 144895-66-9 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2-oxo-1,3-dioxolan-4-yl)acrylate 
• 848566-19-8 (E,4S,5S)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 
• 144895-69-2 (3E,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate 
• 875614-83-8 (E)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-enoate 
• 848566-35-8 (R,E)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-enoate 

Relevant academic research and scientific papers

De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy

A short and highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at

De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate

(Chemical Equation Presented) An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results.