1. A new approach to the synthesis of enantiomerically pure 4-deoxy sugars
- Author
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Romualdo Caputo, Annalisa Guaragna, Giovanni Palumbo, Silvana Pedatella, Francesco Solla, R., Caputo, A., Guaragna, G., Palumbo, Pedatella, Silvana, F., Solla, Caputo, Romualdo, Guaragna, A., Palumbo, Giovanni, Pedatella, S., Solla, F., Guaragna, Annalisa, Silvana, Pedatella, and Francesco, Solla
- Subjects
chemistry.chemical_classification ,Primary (chemistry) ,Double bond ,Stereochemistry ,hexoses ,Organic Chemistry ,Allylic alcohol ,Biochemistry ,Aldehyde ,chemistry ,Electrophile ,monosaccharide ,Moiety ,Cis–trans isomerism - Abstract
In a recent paper2 we have reported the design and synthesis of 3-C-lithiated 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybenzyl)oxy]methane (1) which can be utilized as an allylic alcohol anion equivalent and leads to three-carbon elongations of various electrophiles by introduction of a fully protected hydroxypropenyl moiety. The latter contains a double bond, which can be unravelled to the cis configuration by diastereoselective removal3 of the dimethylene-disulfur bridge, as well as a protected primary hydroxyl group that, depending on the deprotection conditions used (DDQ/NaBH4 or DDQ), may either lead to the free allylic alcohol or to an α,β-unsaturated aldehyde.
- Published
- 2000