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

Helvetica Chimica Acta - Tập 72 Số 6 - Trang 1371-1382 - 1989
Karin Briner1, Andrea Vasella1
1Organisch‐Chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH‐8057 Zürich

Tóm tắt

AbstractA new approach towards the synthesis of glycosides based upon a (formal) insertion of glycosylidene carbenes into O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 I2/Et3N. The diaziridines, the first examples of C‐ alkoxy‐diaziridines, were formed in high yields by the reaction of the [(glycosylidene)‐amino]methanesulfonates 14 and 17–19 with a saturated solution of NH3 in MeOH. The diazirines are highly reactive compounds, losing N2 at room temperature or below. The reaction of the gluco‐configurated diazirine 25 with i‐PrOH yielding a mixture of the α‐ and β‐D‐glucosides 29 and 30 illustrates the potential of glycosylidene‐derived diazirines as a new type of glycosyl donors.

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Helvetica Chimica Acta

Tập 72 Số 6

1371-1382

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