Glycoside synthesis overview

Glycoside Synthesis Based on the Remote Activation Concept An Overview... 

Glycomimetics, 468 Glycoproteins, biosynthesis, 486, 487 Glycosidases, 487, 491, 492 Glycoside synthesis, 381 anomeric selectivity, 382 challenges, 382 via electrochemistry, 385 via electron transfer, 385 inductive effects, 452 miscellaneous methods, 432 new glycosyl donors, 386 orthogonal, 452 overview, 381... 

The use of free radical chemistry at the anomeric center to produce carhon-carhon bonds, especially in an intramolecular fashion, remains a popular method for C-glycoside synthesis. A review entitled C-Glycosidation Technology with Free Radical Reactions appeared in early 1998, and the reader is referred to that somce [2] as well as to the more traditional ones for complete overviews on the subject. Again, the coverage here focuses on the most recent developments. 

Hanessian, S. Glycoside synthesis based on the remote activation concept an overview. In Preparative Carbohydrate Chemistry. Hanessian, S. (ed.) Marcel Dekker New York, 1997, pp. 381-388. 

This article will describe our efforts in the stereoselective synthesis of C-glycosides of biological interest, giving, in the meantime, an overview of the main C-glycosylation procedures and explaining their stereochemistry. 

This chapter provides an updated overview of recent developments in the synthesis of C-glycoside compounds. The stereoselectivity of the C-glycosidation step has improved over recent years, and milder conditions for C—C bond formation are still being developed. The use of unprotected C-glycosides is another important advance that has recently come to fruition [164]. Also the use of modem methods based on metals seems to be increasing in popularity. 

In this article we provide a broad overview of the application of radical methods in carbohydrate chemistry, including typical examples classified by the type of bond formed. The factors controlling the stereoselectivity of inter- and intramolecular C-C bond formation are now well understood and have been exploited in the synthesis of C-glycosides [2]. Intramolecular C C bond formation using carbohydrate-based chiral templates also provides a powerful route to branched-chain sugars [3] and carbocycles [4]. Finally, we include synthetically useful processes involving key carbon-heteroatom and C-H bond formation. 

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