Chen Zhifei, Ning Yibo, Li Lei, Cao Xueying, Xi Gaolei, Cheng Dongxu, Wang Qingfu, Lu Changtong, Yang Kai
Technology Center, China Tobacco Henan Industrial Limited Company Zhengzhou 450002 P. R. China
School of Chemistry and Chemical Engineering, Shandong University of Technology Zibo 255049 P. R. China
RSC Adv. 2025 Feb 10;15(6):4481-4486. doi: 10.1039/d5ra00266d. eCollection 2025 Feb 6.
1,4:3,6-Dianhydro-α-d-glucopyranose (DGP) is one of important biomass pyrolysis anhydro sugar products that derive from the cellulose and hemicellulose components. There is no reliable method for the preparation of DGP at present, which contributed to its high cost with limited market supply and restricted applied research. In this study, we provided a novel method for the synthesis of DGP from methyl 3,6-anhydro-α-d-glucopyranoside for the first time. A mild and environmentally friendly synthetic approach for 3,6-anhydro glucopyranoside was developed the intramolecular cyclization of 6--tosyl glucopyranoside, promoted by a catalytic amount of TBAF. And the preparation of DGP was achieved through the stabilization effect on carbocation intermediates by HFIP in the intramolecular cyclization of 3,6-anhydro glucopyranoside. Further sensory evaluation studies revealed that DGP had a sweetness similar to that of sucrose.
1,4:3,6-二脱水-α-D-吡喃葡萄糖（DGP）是源自纤维素和半纤维素成分的重要生物质热解脱水糖产物之一。目前尚无制备DGP的可靠方法，这导致其成本高昂，市场供应有限且应用研究受限。在本研究中，我们首次提供了一种由3,6-脱水-α-D-吡喃葡萄糖苷合成DGP的新方法。开发了一种温和且环境友好的3,6-脱水吡喃葡萄糖苷合成方法——由催化量的四丁基氟化铵促进的6-对甲苯磺酰基吡喃葡萄糖苷的分子内环化反应。并且通过在3,6-脱水吡喃葡萄糖苷的分子内环化反应中，六氟异丙醇（HFIP）对碳正离子中间体的稳定作用实现了DGP的制备。进一步的感官评价研究表明，DGP具有与蔗糖相似的甜度。
