Abstract
Intramolecular aglycon delivery (IAD) is a specific type of intramolecular glycosylation reaction in which the glycosyl acceptor is first covalently attached, or tethered, to the 2-hydroxyl group of the donor by a short linker. Activation of the glycosyl donor then causes intramolecular glycosylation, which ensures the formation of a 1,2-cis glycosidic linkage with complete control of anomeric stereochemistry. This article summarises the development of IAD, from its inception in the early 1990s, into a reliable and widely applicable method for controlling the stereochemistry of glycosylation. Key to this was the development of IAD based on tethering through the use of common alcohol protecting groups; for example, para-methoxybenzyl (PMB), allyl, and most recently and effectively 2-naphthylmethyl (NAP) ethers. Applications of various types of IAD for the production of a wide range of di- and oligosaccharide materials comprising 1,2-cis glycosidic linkages are reviewed, including the production of N-glycans, furanosides, trehalose and derivatives, and iterative applications of IAD for the synthesis of oligosaccharides that contain multiple 1,2-cis glycosidic linkages. Considerations that are important to maximise reaction efficiency are also discussed.
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