allyl 6-(4-methylbenzenesulfonate)-β-D-glucopyranoside | 223912-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-(4-methylbenzenesulfonate)-β-D-glucopyranoside
• 英文别名: allyl 6-O-tosyl-β-D-glucopyranoside
• CAS: 223912-26-3
• 化学式: C₁₆H₂₂O₈S
• 分子量: 374.412
• InChiKey: LWAAMNZZPGQJKS-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122.52
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 6-(4-methylbenzenesulfonate)-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.5h， 生成 6-azido-2,3,4-tri-O-benzyl-6-deoxy-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties

  摘要：

  Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an alpha-D-glucosyl-(1 -> 4)-beta-D-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6 ''-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.11.017
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 allyl 6-(4-methylbenzenesulfonate)-β-D-glucopyranoside
  参考文献：
  名称：

  A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach

  摘要：

  本文介绍了一种简便灵活的方法，利用级联反应：单击二聚化和闭环偏析，制备含有不同碳水化合物分子的大环分子。

  DOI：

  10.1039/b502682b

文献信息

• Streamlined Iterative Assembly of Thio‐Oligosaccharides by Aqueous <i>S</i> ‐Glycosylation of Diverse Deoxythio Sugars
  作者：Peng Wen、Peijing Jia、Qiuhua Fan、Bethany J. McCarty、Weiping Tang

  DOI：10.1002/cssc.202102483

  日期：2022.2.8

  Step by step: A streamlined practical iterative synthesis of S-oligosaccharides is developed in aqueous solution without the need of protecting any of the hydroxy groups. Various deoxythio sugar building blocks can be prepared efficiently. The Ca(OH)2-promoted aqueous S-glycosylation can be realized with high chemo- and stereoselectivity.

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。
• Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog
  作者：Alexandra Bordes、Ana Poveda、Thibault Troadec、Antonio Franconetti、Ana Ardá、Flavie Perrin、Mickaël Ménand、Matthieu Sollogoub、Jerôme Guillard、Jérôme Désiré、Raphaël Tripier、Jesús Jiménez-Barbero、Yves Blériot

  DOI：10.1021/acs.orglett.0c00503

  日期：2020.3.20

  A new family of chiral C2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4C1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd2+ complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the parent Cd–cyclam complex. Similar behavior is observed

  公开了一种新的手性C 2对称四氮杂大环族，其为IminoSugar Aza-Crown的ISAC，结合了两个采用4 C 1构象的亚氨基糖。在相应的Cd 2+络合物上进行的多核NMR实验表明，ISAC在水中是很强的螯合剂，其四胺腔具有与母体Cd–cyclam络合物相似的构象。在溶液中使用Cu 2+可以观察到类似的行为，与Cu–cyclam配合物相比，稳定性更高。