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

TY - JOUR

T1 - Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

AU - Frihed, Tobias

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - 6-Deoxy-l-sugars

KW - Carbohydrates

KW - Diastereoselectivity

KW - Nucleophilic substitution

KW - Reduction

KW - Substituent effects

U2 - 10.1002/ejoc.201403074

DO - 10.1002/ejoc.201403074

M3 - Journal article

AN - SCOPUS:84919363713

SN - 1434-193X

VL - 2014

SP - 7924

EP - 7939

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -