thio [2-acetamido-2-deoxy-1-thio-β-D-glucopyranose]-(1,1)-S-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside | 5115-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thio [2-acetamido-2-deoxy-1-thio-β-D-glucopyranose]-(1,1)-S-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: Di-(N-acetyl-β-D-glucosaminyl)-disulfid；bis(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranosyl)1,1'-disulfide；N-[(2S,3R,4R,5S,6R)-2-[[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]disulfanyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 5115-92-4
• 化学式: C₁₆H₂₈N₂O₁₀S₂
• 分子量: 472.538
• InChiKey: URIAPNSSDGNNQJ-JSCVLIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  249
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  thio [2-acetamido-2-deoxy-1-thio-β-D-glucopyranose]-(1,1)-S-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 40.0h， 生成 thio {2-acetamido-3,4-di-O-acetyl-6-O-[(tert-butyldimethylsilyl)oxy]-2-deoxy-1-thio-β-D-glucopyranose}-(1,1)-S-2-acetamido-3,4-di-O-acetyl-6-O-[(tert-butyldimethylsilyl)oxy]-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Carbohydrates with an Anomeric Thiol Moiety for Elaboration into Metabolically Stable Thioglycosides

  摘要：

  The synthesis of thioglycosides for use as metabolically stable biological probes is an area of continued interest. This paper describes the synthesis of functionalised carbohydrates which contain an anomeric thio group. During the course of this work we have examined the most viable route into compounds such as the specifically functionalised carbohydrates 36 and 37, and have also investigated the usefulness of disulfides as protecting groups for anomeric thiols.

  DOI：

  10.1080/07328309908544045
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranose 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以72%的产率得到thio [2-acetamido-2-deoxy-1-thio-β-D-glucopyranose]-(1,1)-S-2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Carbohydrates with an Anomeric Thiol Moiety for Elaboration into Metabolically Stable Thioglycosides

  摘要：

  The synthesis of thioglycosides for use as metabolically stable biological probes is an area of continued interest. This paper describes the synthesis of functionalised carbohydrates which contain an anomeric thio group. During the course of this work we have examined the most viable route into compounds such as the specifically functionalised carbohydrates 36 and 37, and have also investigated the usefulness of disulfides as protecting groups for anomeric thiols.

  DOI：

  10.1080/07328309908544045

文献信息

• A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof
  作者：Matteo Adinolfi、Domenica Capasso、Sonia Di Gaetano、Alfonso Iadonisi、Loredana Leone、Antonello Pastore

  DOI：10.1039/c1ob05619k

  日期：——

  Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1′- disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.

  对称的糖基二硫化物可以通过连续反应方法，在几小时内从全乙酰化前体制备得到，期间无需对任何中间体进行纯化。在最后的硫醇盐氧化成二硫化物步骤中，少量的二苯基二硒化物在空气中能显著加速反应。这个策略对非糖类的对称烷基二硫化物的适用性也进行了研究。对一系列合成的1,1'-二硫化物在两种人类肿瘤细胞系上进行了初步的细胞毒性活性测试，结果表明这些化合物具有显著的活性。
• Synthesis of Carbohydrates with an Anomeric Thiol Moiety for Elaboration into Metabolically Stable Thioglycosides
  作者：Milton J. Kiefel、Robin J. Thomson、Milica Radovanovic、Mark von Itzstein

  DOI：10.1080/07328309908544045

  日期：1999.1.1

  The synthesis of thioglycosides for use as metabolically stable biological probes is an area of continued interest. This paper describes the synthesis of functionalised carbohydrates which contain an anomeric thio group. During the course of this work we have examined the most viable route into compounds such as the specifically functionalised carbohydrates 36 and 37, and have also investigated the usefulness of disulfides as protecting groups for anomeric thiols.