We herein introduce glycosyl -phenylethynyl pyrrole-2-carboxylates (PEPCs) as novel and highly efficient glycosyl donors. The unique inclusion of the pyrrole group, serving as both an electron-donating group and an -tethering scaffold, imparts exceptional shelf stability while retaining reactivity for glycosylation reactions. PEPC donors exhibit broad utility for both - and -glycosylation across a variety of substrates. Additionally, their versatility and efficiency were further demonstrated in a one-pot saccharide synthesis, showcasing their potential for diverse synthetic applications.
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Development of Glycosylation Protocols Using Glycosyl -Phenylethynyl Pyrrole-2-carboxylates as Donors.
Org Lett
November 2024
Shanghai Frontiers Science Center of TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
We herein introduce glycosyl -phenylethynyl pyrrole-2-carboxylates (PEPCs) as novel and highly efficient glycosyl donors. The unique inclusion of the pyrrole group, serving as both an electron-donating group and an -tethering scaffold, imparts exceptional shelf stability while retaining reactivity for glycosylation reactions. PEPC donors exhibit broad utility for both - and -glycosylation across a variety of substrates.
View Article and Find Full Text PDFStereoselective synthesis of medium-sized cyclic ethers: application of C-glycosylation chemistry to seven- to nine-membered lactone-derived thioacetals and their sulfone counterparts.
J Org Chem
February 2014
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
Stereoselective synthesis of α,α'-substituted medium-sized cyclic ethers has been achieved by means of nucleophilic substitution of the corresponding lactone-derived thioacetals and their sulfone counterparts. Nucleophilic substitution of medium-sized lactone-derived thioacetals could be achieved efficiently either by (i) activation with NIS/TMSOTf in the presence of allyltrimethylsilane or TMSCN or by (ii) oxidation to the corresponding sulfones followed by treatment with an appropriate organometallic species such as divinylzinc or dimethyl(2-phenylethynyl)aluminum. Interestingly, the stereochemical consequence was found to be largely dependent on the local structure of substrates.
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