SYNTHESIS OF 6-DEOXY-D-ALTROSE USED AS AN AUTHENTIC SAMPLE TO IDENTIFY AN UNKNOWN MONOSACCHARIDE ISOLATED FROM THE FRUITING BODY OF AN EDIBLE MUSHROOM

摘要

Here, we describe the synthesis of 6-deoxy-D-altrose and its subsequent use as an authentic sample to verify the structure of a monosaccharide newly isolated from the fruiting body of an edible mushroom. D-Rhamnopyranoside, converted from D-mannopyranoside, was selectively protected to give the 3-OH derivative, which was converted to the corresponding 6-deoxy-D-altropyranoside by nucleophilic substitution of the 3-triflate with acetoxy group. Removal of the protecting group, including the temporary protection of the anomeric position with the THP group, afforded the desired 6-deoxy-D-altrose. Both the NMR data and the [α]D value were identical to the data on the natural product, thus indicating that the recently isolated monosaccharide was 6-deoxy-D-altrose.