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Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene-derived diaziridines and diazirines

✍ Scribed by Karin Briner; Andrea Vasella

Publisher
John Wiley and Sons
Year
1989
Tongue
German
Weight
858 KB
Volume
72
Category
Article
ISSN
0018-019X

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✦ Synopsis

A new approach towards the synthesis of glycosides based upon a (formal) insertion of glycosylidene carbenes into 0-H bonds is presented. The synthesis and characterization of the glycosylidene-derived diazirines 25-28, precursors of glycosylidene carbenes, are described. The diazirines were prepared by the rapid, high-yielding oxidation of the diaziridines 20 and 22-24 with I,/Et,N. The diaziridines, the first examples of Calkoxy-diaziridines, were formed in high yields by the reaction of the [(glycosylidene)amino]methanesulfonates 14 and 17-19 with a saturated solution of NHj in MeOH. The diazirines are highly reactive compounds, losing N, at room temperature or below. The reaction of the gluco-configurated diazirine 25 with i-PrOH yielding a mixture of the aand fl-D-glucosides 29 and 30 illustrates the potential of glycosylidene-derived diazirines as a new type of glycosyl donors. ') ,) j )

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