Highly efficient multigram synthesis of 1,4:3,6-Dianhydro-α-D-glucopyranose by chemical synthesis methods: Development and scale-up study of synthetic routes

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-01-30 DOI:10.1016/j.carres.2025.109402

Zhi-Fei Chen , Jia-Ming Zhao , Hao-Liang Li , Hao-Yang Chen , Gao-Lei Xi , Liu-Ke Zhang , Qing-Fu Wang , Qiu-Ling Wang , Yong-Zhen Zhao , Kai Yang

引用次数: 0

Abstract

A reliable chemical synthesis method for the preparation of 1,4:3,6-dianhydro-α-D-glucopyranose (DGP) has been developed on the first time, with an overall four-step yield of 20 % on a 200g scale. The method for 2-OH regioselective benzylation protection of Methyl α-d-glucopyranoside was systematically optimized, providing a more scalable and cost-effective approach. The 3,6-anhydro pyranose intermediate was obtained through a two-step one-pot process. It has been confirmed that 2-OH protection enhanced the ring stability of 3,6-anhydro pyranose and also found that the conformation of 3,6-anhydro pyranose indeed promoted the construction of 1,4-ether bonds. Overall, this work facilitated further application research of DGP in the fields of chemical synthesis, medicinal chemistry, and food chemistry.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".