Chemical Glycosylation with p‑Methoxyphenyl (PMP) Glycosides via Oxidative Activation

A novel persulfate-mediated oxidative glycosylation system using p-methoxyphenyl (PMP) glycosides as bench-stable glycosyl donors is developed. This study shows that both K2S2O8 as an oxidant and Hf­(OTf)4 as a Lewis acid catalyst play important roles in the oxidative activation of the PMP group int...

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Published in:Organic letters 2023-05, Vol.25 (19), p.3471-3475
Main Authors: Kim, Hyun Su, Jang, Eunbin, Kim, Hoe In, Hari Babu, Madala, Lee, Jae-Young, Kim, Sang Kyum, Sim, Jaehoon
Format: Article
Language:English
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Summary:A novel persulfate-mediated oxidative glycosylation system using p-methoxyphenyl (PMP) glycosides as bench-stable glycosyl donors is developed. This study shows that both K2S2O8 as an oxidant and Hf­(OTf)4 as a Lewis acid catalyst play important roles in the oxidative activation of the PMP group into a potential leaving group. This convenient glycosylation protocol proceeds under mild conditions and delivers a wide range of biologically and synthetically valuable glycoconjugates, including glycosyl fluorides.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01050