Synthesis of methyl alpha- and beta-D-xylopyranoside-5-18O.


Methyl alpha- and beta-D-xylopyranoside-5-18O (5 and 6) were prepared by way of oxygen exchange between 18O-water and the periodate-oxidation product (1) obtained from 1,2-O-isopropylidene-alpha-D-glucofuranose. The isotopic enrichment of 5 and 6 was determined by hydrolysis of each to D-xylose-5-18O (3), conversion of the sugar into 1,2,3,4-tetrakis-O-(tert-butyldimethylsilyl)-beta-D-xylopyranose-5-18O (7), and determination of the 18O content of the latter by use of a quadrupole, mass spectrometer.

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@article{Hitz1976SynthesisOM, title={Synthesis of methyl alpha- and beta-D-xylopyranoside-5-18O.}, author={William D. Hitz and Daniel C. Wright and Paul A. Seib and Michael K. Hoffman}, journal={Carbohydrate research}, year={1976}, volume={46 2}, pages={195-200} }