2-benzimidazolyl 1-thio-β-D-galactofuranoside | 514847-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzimidazolyl 1-thio-β-D-galactofuranoside
• 英文别名: (2S,3R,4R,5S)-2-(1H-benzimidazol-2-ylsulfanyl)-5-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• CAS: 514847-46-2
• 化学式: C₁₃H₁₆N₂O₅S
• 分子量: 312.346
• InChiKey: XZKMHKUWMFCFPQ-JCIQBVFBSA-N

物化性质

• 沸点：
  702.4±70.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  144
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-benzimidazolyl 1-thio-β-D-galactofuranoside 在 磷酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 D-galactofuranosyl 1-phosphate
  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
• 作为产物：
  描述：

  benzimidazol-2-yl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到2-benzimidazolyl 1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  使用未保护的1-硫代亚氨酰基六呋喃糖苷的一步法合成游离的呋喃呋喃糖基1-磷酸盐

  摘要：

  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。

  DOI：

  10.1021/jo0484934

文献信息

• Improvement of the versatility of an arabinofuranosidase against galactofuranose for the synthesis of galactofuranoconjugates
  作者：Quentin Pavic、Aline Pillot、Olivier Tasseau、Laurent Legentil、Sylvain Tranchimand

  DOI：10.1039/c9ob01162e

  日期：——

  syntheses but the use of galactofuranosidase has not been described yet for the synthesis of galactofuranoconjugates. Interestingly CtAraf51, an α-l-arabinofuranosidase from Ruminiclostridium thermocellum, is able to use aryl- or alkyl-β-d-galactofuranosides as the substrate but with very low efficiency. To allow its use as a synthesis tool, we decided to improve the efficiency of this enzyme toward these non-natural

  半乳糖呋喃共轭物是具有令人感兴趣的生物学特性的稀有化合物。然而，通过传统方法进行的合成是乏味的。如今，糖苷酶经常用于简化此类合成，但尚未描述使用半乳糖呋喃糖苷酶合成半乳糖醛酸缀合物。有趣的是，CtAraf51，一种来自热细单胞菌的α-1-1-阿拉伯呋喃糖苷酶，能够使用芳基-或烷基-β-d-d-半乳糖呋喃糖苷作为底物，但是效率非常低。为了将其用作合成工具，我们决定提高该酶对这些非天然底物的效率。首先，我们确定了三个残基，这些残基可能导致与对硝基苯基-β-d-半乳糖呋喃糖苷的不利相互作用。诱变后 两个突变体的催化效率分别比野生型高四倍和三倍。然后使用乙醇作为模型受体底物在转糖基化反应中评估这两个突变体。在这些条件下，一个突变体的效率要高得多：50％的转化率是野生型的十倍。最终，两个突变体都转化为硫代糖醇：在硫基化反应中，该反应比单个E173A突变体快两倍，在酰化反应中，初始速度提高了四倍。所得突变体合成各种O-，
• 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.
• Versatile Synthesis of Rare Nucleotide Furanoses
  作者：Pauline Peltier、Richard Daniellou、Caroline Nugier-Chauvin、Vincent Ferrières

  DOI：10.1021/ol702392x

  日期：2007.12.1

  Direct activation of unprotected thioimidoyl furanosides yielded in only one step and few minutes a panel of rare uridine 5'-diphosphofuranoses. Diastereoselectivity of the reaction was tightly connected with reaction time, temperature, and nature of the furanosyl donor. This approach was totally selective since no ring expansion from the initial five-membered ring to the more stable pyranose form was observed.
• 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.