Summary
Readily available β-glycofuranosyl isocyanides1,2,4,5,6,18,19,20 are transformed into the corresponding protected tetrahydrofurans21,22,23,24,25,26 by means of tributyltin hydride andAIBN. The synthesis of18 and19 by dehydration of the formamide15 is described. Starting with 6-deoxy-1,2-O-isopropyliden-α-D-allofuranose (7) crystalline 1,2-O-diacetyl-3,5-dibenzoyl-β-D-allofuranose (9) is obtained.9 is first transformed into the anomeric azides11,12 and13,14 and subsequently into the formamide15.
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Hiebl, J., Zbiral, E. Transformationen von β-Glycofuranosylisocyaniden in Tetrahydrofuranderivate. Monatsh Chem 121, 683–690 (1990). https://doi.org/10.1007/BF00809773
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DOI: https://doi.org/10.1007/BF00809773