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Published on: July 6, 2012
Chemical Glycosylation with p-Methoxyphenyl (PMP) Glycosides via Oxidative Activation
Hyun Su Kim1, Eunbin Jang2, Hoe In Kim2
1College of Pharmacy, CHA University, 120 Haeryong-ro, Pocheon-si, Gyeonggi-do 11160, Republic of Korea.
Abstract:
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.
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