1132966-47-2Relevant academic research and scientific papers
Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate
He, Haiqing,Chen, Dong,Li, Xiaomei,Li, Chengji,Zhao, Jin-Hua,Qin, Hong-Bo
, p. 2877 - 2882 (2019)
We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl
Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid
Bedini, Emiliano,Iadonisi, Alfonso,Silipo, Alba,Traboni, Serena,Vessella, Giulia
, p. 5669 - 5676 (2021/11/11)
The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per-O-acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2-trans stereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non-trivial glycosides with applicable potential.
An investigation of construction of chondroitin sulfate E (CS-E) repeating unit
Yang, Shuang,Wang, A-peng,Zhang, Guangyan,Di, Xiangjie,Zhao, Zhehui,Lei, Pingsheng
, p. 5659 - 5670 (2016/08/23)
A series of the derivatives of chondroitin sulfate E (CS-E) disaccharide repeating unit were prepared by postglycosylation–oxidation strategy. The strategy showed excellent performance in glycosylation both on the reactivity and stereoselectivity. Different protecting methodologies were used for the manipulation of disaccharide building blocks. Substitutes at C-4 of glucosyl donors mildly influenced the glycosylation. The current synthesis afforded a feasible approach for the preparation of CS-E repeating unit.
Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus
Mukherjee, Chinmoy,Misra, Anup Kumar
experimental part, p. 2746 - 2751 (2009/04/07)
The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain d-galactosamine moiety with an (S)-configuration was formed exclusively.
