Few studies have been done to dissect the individual contributions of protecting groups to the stereoselectivity of glycosylation reactions in furanosides.  Model compounds are not readily available or are prohibitively expensive.  We present a three step synthesis using cheap starting materials to generate 3,4-dihydroxybutaldehyde.  The hydroxyl moieties of 1,2,4-butanetriol are selectively protected at positions 1 and 2 as an isopropylidene acetal.  The unprotected alcohol is then oxidized to the aldehyde under green conditions with a hetereogeneous TEMPO catalyst.  After hydrolysis of the acetal, this product can then be protected with a variety of protecting groups and used as model compounds for stereoselectivity studies for glycosylation with furanosides.

New multistep synthesis for organic chemistry labs: Applications in carbohydrate stereochemistry

241st National Meeting (2011)

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