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

被引：0

作者：

Chen, Zhi-Fei ^{[1
]}

Zhao, Jia-Ming ^{[1
]}

Li, Hao-Liang ^{[1
]}

Chen, Hao-Yang ^{[1
]}

Xi, Gao-Lei ^{[1
]}

Zhang, Liu-Ke ^{[1
]}

Wang, Qing-Fu ^{[1
]}

Wang, Qiu-Ling ^{[1
]}

Zhao, Yong-Zhen ^{[1
]}

Yang, Kai ^{[2
]}

机构：

[1] China Tobacco Henan Ind Ltd Co, Technol Ctr, Zhengzhou 450002, Peoples R China

[2] Shandong Univ Technol, Sch Chem & Chem Engn, Zibo 255049, Peoples R China

来源：

CARBOHYDRATE RESEARCH | 2025年 / 551卷

关键词：

MEDIATED REGIOSELECTIVE BENZYLATION; REACTIVITY; MECHANISM; POLYOLS; DIOLS; ACID;

D O I：

10.1016/j.carres.2025.109402

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A reliable chemical synthesis method for the preparation of 1,4:3,6-dianhydro-alpha-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 alpha-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 2OH 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.

引用

页数：6

共 26 条

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