S-o-(p-Methoxyphenylethynyl)benzyl (SMPEB) Glycosides for Catalytic Glycosylation and Their Application in the Synthesis of Polyporus Umbellatus Polysaccharides

Abstract

We herein reported a new type of S-o-(pmethoxyphenylethynyl)benzyl donor for a highly efficient glycosylation method. The donor was activated by 10% Tf 2 O and underwent glycosylation with various acceptors to provide the corresponding glycosides in excellent yield. Furthermore, two repetitive fragments of Polyporus umbellatus polysaccharides (PUPs), isolated from traditional Chinese medicine "Polyporus umbellatus", were prepared by combining the "single-catalyst onepot" and "latent-active" strategies for the first time for future clear studies on the structure−activity relationship of PUPs.

Efficient O- and S-glycosylation with ortho-2,2-dimethoxycarbonylcyclopropylbenzyl thioglycoside donors by catalytic strain-release

“…However, it was only in the past decade that a handful of successful examples were reported, predominantly centered around the well-established alkyne or alkene chemistry hinging on Au( i ) or superacid catalysis, pioneered by the groups of Yu 17 and Ragains, 18,19 respectively. These methods were subsequently carried forward and glorified by the groups of Zhu, 20 Sun, 21 Li, 22 and Chai, 23 whose elegant protocols significantly expanded the donor and acceptor scopes of catalytic glycosylation of thioglycosides (Fig. 1D).…”