Medicinal chemistry oligosaccharide synthesi

An important aspect of this approach is the ease with which fiiran alcohols can be prepared in enantiomerically pure form from achiral furans (e.g., 7 and 8). There are many asymmetric approaches to prepare furan alcohols. The two most prevalent approaches are (i) the Noyori reduction ofacylfurans (8 to 12) and (ii) the Sharpless dihydroxylation of vinyUurans (7 to 12) (Scheme 1.4) [17]. Both routes are readily adapted to 100 g scale synthesis and use readily available reagents. While the Sharpless route is most amenable to the synthesis of hexoses with a C-6 hydroxy group, the Noyori route distinguishes itself in its flexibility to virtually any substitution at the C-6 position. Herein, we review the development of the Achmatowicz approach to the de novo synthesis of carbohydrates, with apphcation to oligosaccharide assembly and medicinal chemistry studies. 

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