Stereoselective Synthesis of ß-glycosyl Esters via 1-Hydroxybenzotriazole Mediated Acylation of Glycosyl Hemiacetals.

Liu, Zijing; Liu, Dan; Zhu, Dapeng; Yu, Biao

Liu, Zijing; Liu, Dan; Zhu, Dapeng; Yu, Biao.

Afiliación

Liu Z; Key Laboratory of Structure-Based Drugs Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
Liu D; State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
Zhu D; Key Laboratory of Structure-Based Drugs Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
Yu B; Institute of Translational Medicine, Shanghai Jiao Tong University, Shanghai 200240, China.

Org Lett ; 25(28): 5372-5377, 2023 Jul 21.

Article en En | MEDLINE | ID: mdl-37436734

RESUMEN

Highly stereoselective access to ß-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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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2023 Tipo del documento: Article País de afiliación: China

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