1139852-98-4Relevant academic research and scientific papers
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.
Selective acetolysis of primary benzyl groups in carbohydrate derivatives under the mild reaction condition
Kundu, Monalisa,Misra, Anup Kumar
, (2019/10/16)
Selective acetolysis of the primary benzyloxy groups in a wide variety of carbohydrate derivatives was achieved in excellent yield using acetic anhydride and perchloric acid supported over silica (HClO4–SiO2) as a solid acid catalyst
Preparation method, intermediate and application of fucosylated chondroitin sulfate trisaccharide
-
, (2019/07/04)
The invention discloses a synthesizing method of a fucosylated chondroitin sulfate trisaccharide repeat unit. The synthesizing method takes beta-penta-acetyl glucose, D-galactosamine hydrochloride andL-fucose, which are easy to acquire, as raw materials t
Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate
He, Haiqing,Chen, Dong,Li, Xiaomei,Li, Chengji,Zhao, Jin-Hua,Qin, Hong-Bo
supporting information, p. 2877 - 2882 (2019/03/21)
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
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.
