Synthesis of rare carbohydrates and analogues starting from enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives ("naked sugars")

Vogel, P.2005-11-092005-11-092005-11-09200010.2174/1385272003376175https://infoscience.epfl.ch/handle/20.500.14299/219772Recent applications of the "naked sugar" methodology are reviewed. General methods have been developed to transform enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives into rare monosaccharides, carbasugars, into a new doubly-branched imino-dideoxyalditol (iminosugar), into long-chain carbohydrates, C-disaccharides, imino-C-disaccharides and new polyhydroxylated quinolizidines. The methods allow to prepare both enantiomers of a given target with the same ease. Predictable high stereoselectivity of the reactions of the bicyclic chirons adds to the flexibility of the approach that can lead to a large molecular diversity.Aza-c-disaccharidesalpha-glucosidase-ibeta-d-xylosideelectrondonating substituentvenous antithrombotic agentschondroitin sulfatechainstotal asymmetric-synthesisefficient total synthesisring-expanded analogsdiels-alder additionsSynthesis of rare carbohydrates and analogues starting from enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives ("naked sugars")text::journal::journal article::research article