2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranose | 1283073-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranose
• 英文别名: Glc2Ac3Ac4Ac6Ac(b1-3)b-Glc1SH2Ac4Ac6Ac；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-sulfanyloxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1283073-63-1
• 化学式: C₂₆H₃₆O₁₇S
• 分子量: 652.628
• InChiKey: ASFNWDASYOSXSM-VRECAULFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  213
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranose 在 氢溴酸 、 sodium hydride 、 溶剂黄146 、 1,7-偶氮-15-冠-5 、 巯基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.17h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-3-deoxy-(1→3)-dithio-β-D-glucopyranose
  参考文献：
  名称：

  Oligo-β-(1 → 3)-glucans: Impact of Thio-Bridges on Immunostimulating Activities and the Development of Cancer Stem Cells

  摘要：

  Recent developments of innovative anticancer therapies are based on compounds likely to stimulate the immune defense of the patients. beta-(1 -> 3)-Glucans are natural polysaccharides well-known for their immunostimulating properties. We report here on the synthesis of small oligo-beta-(1 ? 3)-glucans characterized by thioglycosidic linkages. The presence of sulfur atom(s) was not only crucial to prolong in vivo immunoactive activities in time, compared to native polysaccharides, but sulfur atoms also had a direct impact on the development of colorectal cancer stem cells. As a result, a short, pure, and structurally well-defined trisaccharidic thioglucan demonstrated similar activities compared to those of natural laminarin.

  DOI：

  10.1021/jm500506b
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranose 在 氢溴酸 、 溶剂黄146 、 巯基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.17h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Oligo-β-(1 → 3)-glucans: Impact of Thio-Bridges on Immunostimulating Activities and the Development of Cancer Stem Cells

  摘要：

  Recent developments of innovative anticancer therapies are based on compounds likely to stimulate the immune defense of the patients. beta-(1 -> 3)-Glucans are natural polysaccharides well-known for their immunostimulating properties. We report here on the synthesis of small oligo-beta-(1 ? 3)-glucans characterized by thioglycosidic linkages. The presence of sulfur atom(s) was not only crucial to prolong in vivo immunoactive activities in time, compared to native polysaccharides, but sulfur atoms also had a direct impact on the development of colorectal cancer stem cells. As a result, a short, pure, and structurally well-defined trisaccharidic thioglucan demonstrated similar activities compared to those of natural laminarin.

  DOI：

  10.1021/jm500506b

文献信息

• Protecting Group-Free Glycoligation by the Desulfurative Rearrangement of Allylic Disulfides as a Means of Assembly of Oligosaccharide Mimetics
  作者：Venkataraman Subramanian、Myriame Moumé-Pymbock、Tianshun Hu、David Crich

  DOI：10.1021/jo102411j

  日期：2011.5.20

  2-(2-Pyridyldithio-3-butenyl) glycosides react with carbohydrate-based thiols in a two-step process involving sulfenyl transfer followed by desulfurative 2,3-allylic rearrangement, promoted by either triphenylphosphine or silver nitrate, to give novel saccharide mimetics. In an alternative embodiment of the same chemistry anomeric thiols are coupled with carbohydrates derivatized in the form of 2-

  2-(2-Pyridyldithio-3-butenyl) 糖苷与基于碳水化合物的硫醇在两步过程中反应，包括硫基转移，然后脱硫 2,3-烯丙基重排，由三苯基膦或硝酸银促进，得到新型糖类模拟物. 在相同化学异头硫醇的替代实施方案中，与以2-(2-吡啶基二硫代-3-丁烯基)醚形式衍生的碳水化合物偶联。这种新的糖基化方法不需要保护羟基，并且与乙酰胺、叠氮化物、三氯乙氧基氨基甲酸酯和硫糖苷的存在兼容。通用主题的变化使得能够制备还原性和非还原性寡糖以及非糖苷连接系统的模拟物。
• Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature
  作者：Yao Liu、Xiao-Bing Yu、Xiang-Mei Zhang、Qian Zhong、Li-Hua Liao、Nan Yan

  DOI：10.1039/d1ra04013h

  日期：——

  transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presented via arynes generated in situ combined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction

  在 TBAF( t BuOH) 4存在下，通过原位生成的芳烃与糖基硫醇结合，提出了一种温和、方便且不含过渡金属的芳基 1-硫糖苷合成方案。该方法提供了一种通用且有效的方法来制备一系列功能化的硫糖苷，并在室温下完美控制异头构型。此外，反应条件耐受多种戊糖和己糖，反应在受保护的单糖和二糖上也能顺利进行。