Efficient Two Step β-Glycoside Synthesis from N-Acetyl D-Glucosamine: Scope and Limitations of Copper(II) Triflate-Catalyzed Glycosylation

被引：8

作者：

Sommer, Roman ^{[1
,2
]}

Hauck, Dirk ^{[1
,2
]}

Titz, Alexander ^{[1
,2
]}

机构：

[1] Helmholtz Inst Pharmaceut Res Saarland HIPS, Campus E 8-1, D-66123 Saarbrucken, Germany

[2] Deutsch Zentrum Infekt Forsch DZIF, Standort Hannover Brauns, Germany

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 15期

关键词：

alpha-glycosides; beta-glycosides; copper(II) triflate; glycosylation; N-acetyl glucosamine; DONORS;

D O I：

10.1002/slct.201700161

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

beta-Linked glycosides of N-acetyl glucosamine are widespread in nature. Their direct synthesis is hampered by the low reactivity of GlcNAc as a glycosyl donor. We report a selective and rapid copper(II) triflate-catalyzed two-step synthesis of beta-glycosides of GlcNAc from cheap GlcNAc as starting material without purification of intermediates. alpha-Specific glycosylation can be achieved by increasing the amount of catalyst and extending reaction times.

引用

页码：4187 / 4192

页数：6

共 3 条

[1] D-Glucosamine as an efficient ligand for the copper-catalyzed selective synthesis of anilines from aryl halides and NaN3
Thakur, Krishna Gopal
Srinivas, Kotha Surya
Chiranjeevi, Korupalli
Sekar, Govindasamy
[J]. GREEN CHEMISTRY, 2011, 13 (09) : 2326 - 2329
[2] Development of a two-enzyme system in Aspergillus niger for efficient production of N-acetyl-β-D-glucosamine from powdery chitin
Han, Susu
Xue, Yibin
Yan, Qiaojuan
Jiang, Zhengqiang
Yang, Shaoqing
[J]. BIORESOURCE TECHNOLOGY, 2024, 393
[3] Copper(II) triflate-catalyzed highly efficient synthesis of N-substituted 1,4-dihydropyridine derivatives via three-component cyclizations of alkynes, amines, and α,β-unsaturated aldehydes
Li, Sifeng
Yang, Qingjing
Wang, Jun
[J]. TETRAHEDRON LETTERS, 2016, 57 (40) : 4500 - 4504

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