Photochemical Glycosylation

Document Type

Article

Publication Date

3-9-2017

Abstract

The field of chemical glycosylation is one that is often criticized for the development of harsh conditions. Photochemical glycosylations involving singlet glycosylidene donors result from the irradiation of substrates including cyclobutanones and glycosyldiazirines. On the other hand, a number of photochemical glycosylations involve the use of chromophore-containing additives known as photosensitizers. This chapter discusses many of the glycosylations that are involved in excitation of photosensitizers by absorption of a photon, a series of electron transfers to and from the excited-state photosensitizer, and regeneration of the photosensitizer. Chalcogenoglycosides including thioglycosides and selenoglycosides are popular glycosyl donors among synthetic chemists. The synthesis of C-glycosides using photosensitization, photoinitiation, or direct irradiation of the glycosyl donor has been the subject of fairly extensive development relative to photochemical O-glycosylation. Singlet glycosylidenes and metalloglycosylidenes have been the subjects of some of this development.

Publication Source (Journal or Book title)

Selective Glycosylation Synthetic Methods and Catalysts

First Page

211

Last Page

230

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