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Stereoselective Synthesis of β-glycosyl Esters via 1-Hydroxybenzotriazole Mediated Acylation of Glycosyl Hemiacetals. 2023
Key Laboratory of Structure-Based Drugs Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
Highly stereoselective access to β-glycosyl esters was disclosed, employing 1-hydroxybenzotriazole (HOBt) mediated esterification of glycosyl hemiacetals in the presence of EDCI and 1,4-diazabicyclo[2.2.2]octane (DABCO). Mechanistic studies indicated a dynamic kinetic acylation pathway. In addition, a stereoretentive esterification of glycosyl hemiacetals with tert-butyloxycarbonyl ortho-hexynylbenzoate and DMAP was also reported.
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