Tetrahedron letters2022，Vol.916.DOI:10.1016/j.tetlet.2022.153638

An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis

Yi, Yanliang Ma, Xinyuan Liu, Ruiwen Chu, Xindang Li, Haiwei Zhang, Jiayi Gao, Qianqian Zhang, Yongmin Zhang, Lihe Zhou, Demin Xiao, Sulong
Tetrahedron letters2022，Vol.916.DOI:10.1016/j.tetlet.2022.153638
✕
  • NSTL
  • Elsevier

An attempt to synthesize the two monomers of CDTOH: Unexpected NMR and X-ray diffraction crystal analysis

Yi, Yanliang 1Ma, Xinyuan 1Liu, Ruiwen 1Chu, Xindang 1Li, Haiwei 1Zhang, Jiayi 1Gao, Qianqian 1Zhang, Yongmin 2Zhang, Lihe 1Zhou, Demin 1Xiao, Sulong1
扫码查看

作者信息

  • 1. Peking Univ
  • 2. Sorbonne Univ
  • 折叠

Abstract

Two monomer compounds of CDTOH, 6(A)-deoxy-6(A)-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)-per-O-methylated beta-cyclodextrin 4 and 6(A)-deoxy-6(A)-(4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl) beta-cyclodextrin 7, have been synthesized via click chemistry. The structures were confirmed by H-1 NMR, C-13 NMR and ESI-HRMS. In comparison to the 1H NMR spectra of compound 4 and intermediate 6, two sets of peaks in the high field of 7 are somewhat unusual. The X-ray single-crystal analysis of 7 showed the existence of an intramolecular hydrogen bond between the CH2OH donor of glucose B and the terminal hydroxy acceptor of the side chain, leading to the 4-(2-hydroxyethyl)-1H-1,2,3-triazole group protruding outside the cavity and embedding in the hydrophobic cavity of the adjacent molecule (interinclusion) to form an interlocked helical columnar superstructure. (C) 2022 Elsevier Ltd. All rights reserved.

Key words

CDTOH/beta-cyclodextrin/Crystal structure/Click chemistry/Interinclusion

引用本文复制引用

出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
被引量1
参考文献量15
段落导航相关论文