2-benzothiazolyl 1-thio-β-D-galactofuranoside | 514847-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzothiazolyl 1-thio-β-D-galactofuranoside
• 英文别名: (2S,3R,4R,5S)-2-(1,3-benzothiazol-2-ylsulfanyl)-5-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• CAS: 514847-47-3
• 化学式: C₁₃H₁₅NO₅S₂
• 分子量: 329.398
• InChiKey: KOUHTQHUNIVICK-RPWYLVQBSA-N

物化性质

• 沸点：
  651.7±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  辛醇 、 2-benzothiazolyl 1-thio-β-D-galactofuranoside 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 n-octyl α-D-galactofuranoside 、 octyl β-D-galactofuranoside
  参考文献：
  名称：

  First O-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations

  摘要：

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.

  DOI：

  10.1021/jo070741j
• 作为产物：
  描述：

  benzothiazol-2-yl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 甲醇 、 sodium methylate 作用下， 以72%的产率得到2-benzothiazolyl 1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  A novel synthesis of d-galactofuranosyl, d-glucofuranosyl and d-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors

  摘要：

  The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00822-3

文献信息

• General One-Step Synthesis of Free Hexofuranosyl 1-Phosphates Using Unprotected 1-Thioimidoyl Hexofuranosides
  作者：Ronan Euzen、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo0484934

  日期：2005.2.1

  synthesis of hexofuranosyl 1-phosphates starting from new unprotected glycofuranosyl donors. It required first the preparation of new 1-thiohexofuranosides bearing a thioimidoyl heterocycle as a leaving group. The presence of sulfur and/or nitrogen atom(s) on the aglycon allowed remote activation of these thioglycofuranosides by anhydrous phosphoric acid and led to the target phosphates 9, 27, 29, and 30

  从新的未保护的糖呋喃糖基供体开始，开发了用于合成呋喃糖基1-磷酸酯的一般的一步策略。它首先需要制备带有硫代酰亚胺基杂环作为离去基团的新的1-硫己呋喃呋喃糖苷。硫和/或氮原子（一个或多个）上的糖苷配基的存在使得这些thioglycofuranosides的远程激活通过无水磷酸，并导致目标磷酸盐9，27，29，和30具有良好的选择性至极好的选择性，更重要的是，环扩展非常有限或没有。此外，通过避免对带负电荷的化合物进行任何繁琐的保护基操作并着重于简单但通用的纯化程序，可以显着改善这一一步的磷酸化反应。该方法被用于d-半乳糖和d-呋喃呋喃糖基1-磷酸的非对映控制合成，还用于制备稀有的差向异构体和/或脱氧对应物，即d-甘露糖醛和d-呋喃呋喃糖基衍生物。
• A novel synthesis of d-galactofuranosyl, d-glucofuranosyl and d-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors
  作者：Vincent Ferrières、Sophie Blanchard、Delphine Fischer、Daniel Plusquellec

  DOI：10.1016/s0960-894x(02)00822-3

  日期：2002.12

  The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.
• First <i>O</i>-Glycosylation from Unprotected 1-Thioimidoyl Hexofuranosides Assisted by Divalent Cations
  作者：Ronan Euzen、Jean-Paul Guégan、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo070741j

  日期：2007.7.1

  The preparation of O-hexofuranosides was accomplished from unprotected 1-thioimidoyl furanosides as donors. The present methodology was first used for the synthesis of octyl galactofuranoside and further extended to D-galactofuranose-containing disaccharides. Within this study, we emphasized the need for additional complexing cations to maintain the furanose ring in its initial size. After experimentation, calcium ion was first used concomitantly with trimethylsilyl trifluoromethanesulfonate, the latter being able to activate the thioimidate and the former being likely to inhibit ring expansion. Moreover, an improvement was performed by using copper(II) trifluoromethanesulfonate which could then meet the requirements as both promoter and complexing agent.