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Glycosyl o-1-phenylenyl benzoate: a universal glycosyl donor for the efficient synthesis of oxyglyco
Glycosides oxyglycosides (O-glycosides) and nucleosides (N-glycosides) play very important roles in many life processes. Chemical synthesis is an efficient and scalable method to obtain structurally defined and pure glycoconjugates, which allows an in-depth understanding of their functions and the development of new therapeutic agents. However, the development of efficient synthesis of glycosidization reactions applicable to both oxyglycosides and nucleosides has been a long-standing challenge in chemistry.
In 2008, Yu Biao's group at Shanghai Institute of Organic Chemistry (SIOC) developed glycosyl o-alkynyl benzoate (ABz) as a novel glycosyl donor for the chemical synthesis of both oxyglycosides and nucleosides, and successfully applied it to the total synthesis of many complex glycan natural products with important physiological activities. Nowadays, this glycosidation reaction is internationally known as Yu glycosylation.In early 2019, Yu Biao's group reported a new glycosidation reaction based on the ether bond type, which can also realize the efficient synthesis of oxyglycosides and nucleosides. Although important breakthroughs have been made in this field, challenges remain. For example, there are still very limited methods for glycosidation reactions with easy-to-prepare and stable glycosyl donors, inexpensive and readily available promoters, and mild reaction conditions. The number of glycosyl donors that can be combined to perform multi-step, one-pot glycosidation reactions remains scarce. In addition, generalized glycosidation reaction methods that can achieve the efficient synthesis of oxyglycosides and nucleosides at lower cost for industrial applications are still extremely rare. Recently, a new general-purpose glycosidization reaction method has been reported by a domestic group, which can realize the efficient synthesis of oxyglycosides and nucleosides.
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