215544-02-8

Upstream product

• 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 
• 90661-39-5 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 

Downstream Products

• 848566-24-5 (3S,4S,5R)-5-(2'-benzyloxy-(1'S)-1'-hydroxy-ethyl)-3,4-dihydroxy-dihydro-furan-2(3H)-one 

Relevant academic research and scientific papers

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.

Asymmetric syntheses of chiral allylic alcohols

Chiral allylic alcohols 2 can easily be obtained by elimination from iodo ketals 10. These are available from natural sources, or by application of the asymmetric Sharpless dihydroxylation to vinylogous esters 6, subsequent reduction, halogenation and elimination. This protocol allows the synthesis of highly functionalized allylic alcohols, which can be used in asymmetric Claisen rearrangements.