Rapid and efficient conversion of sialyl thioglycosides to sialyl esters via NIS/BF3OEt2-promoted glycosylation |
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Authors: | Jiazhe Wang Rongkun Liu You Yang |
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Institution: | Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China |
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Abstract: | A rapid and efficient one-step conversion of sialyl thioglycosides to sialyl esters was disclosed. Under the promotion of NIS and BF3OEt2, the glycosylation of per-acetylated sialyl thioglycoside with a set of carboxylic acids provided β-sialyl esters as the major products in good to excellent yields within 5 min. Compared with the long-chain alkyl-, aryl- and α,β-unsaturated acids, complete β-selectivities were observed when the short-chain alkyl acids were selected as the coupling partners. The resultant β-selectivity for the glycosylation of the per-acetylated sialyl thioglycoside with acetic acid was compromised when the 5-N,4-O-oxazolidinone protected sialyl thioglycoside was employed as the coupling partner. |
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Keywords: | Glycosylation Sialyl esters Sialyl thioglycosides Synthetic methods |
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