Some Aspects of Selectivity in the Reaction of Glycosyl Donors*

* Dedicated to the memory of Professor Jacques van Boom.

Abstract

Some advantages, disadvantages, and anomalies of various donors in glycosidations are discussed. By studying several two‐component donor/acceptor‐diol reactions, it is shown that regiopreferences are not very sensitive to the type of donor used. However, in competitive glycosidations within a given type of donor and between different types of donor, it is shown that regio‐ and chemoselectivities must be indexed to donor reactivity.

* Dedicated to the memory of Professor Jacques van Boom.

Keywords:

• Chemo and regioselectivity in glycosylation
• Donors in armed/disarmed competitive glycosylations

Acknowledgments

B.F.R. is grateful to the National Science Foundation (CHE‐0236946) and the Mizutani Foundation of Japan for partial support of this work. J.C.L. and A.M.G. are grateful to the Dirección General de Enseñanza Superior (Grant: PPQ2003‐00396) and the Ministerio de Ciencia y Tecnología for financial support. C.U. thanks the CSIC for financial support.

Notes

* Dedicated to the memory of Professor Jacques van Boom.