Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

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The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4-oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.

OriginalsprogEngelsk
TidsskriftEuropean Journal of Organic Chemistry
Vol/bind2014
Udgave nummer35
Sider (fra-til)7924-7939
Antal sider16
ISSN1434-193X
DOI
StatusUdgivet - 2014

ID: 131020797