D-Tagatose is one of the 2-ketohexoses and a member of rare sugars, which rarely occurs in nature.  Since D-tagatose possesses interesting features such as suppressing postprandial blood glucose level, derivatization of D-tagatose is also important issue for developing their functionalities.  We plan to synthesize α-D-tagatofuranoside by stereoselective glycosidation of 3,4-O-isopropylidene-protected tagatofuranose.  The glycosyl donor was synthesized from D-tagatose in 5 steps with glycosyl phthalate leaving group.  Glycosylation of the synthesized D-tagatofuranosyl donor with various glycosyl acceptor such as primary alcohol, phenol, menthol, etc., took place smoothly to afford α-glycosides as a sole product.  Stereochemical assignment of the anomeric position was done by noesy experiment as well as comparison of chemical shift of carbon-13 NMR.  Glycosidation of D-tagatofuranosyl donor with D-glucose and D-mannose were also examined to give D-tagatofuranosyl disaccharides with α-selectivities.

α-Selective glycosidation of D-tagatofuranose using 3,4-O-isopropylidene protection

2019 Fall National Meeting

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