phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide | 197631-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide
• 英文别名: (2R,3S,4S,5R,6R)-2-(benzenesulfinyl)-3,4,5-trimethoxy-6-(methoxymethyl)oxane
• CAS: 197631-81-5
• 化学式: C₁₆H₂₄O₆S
• 分子量: 344.429
• InChiKey: QOSRDJGTZGPDCZ-XDVLKZDYSA-N

物化性质

• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷-D2 为溶剂， 生成 trifluoromethanesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and ¹H, ¹³C, and ¹⁹F NMR Spectroscopic Investigation

  摘要：

  The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

  DOI：

  10.1021/ja971239r
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside S-oxide
  参考文献：
  名称：

  通过Cp2ZrCl2 / AgClO4介导的异头亚砜的糖基化。

  摘要：

  DOI：

  10.1021/jo015952h

文献信息

• Exploring the Far Side of Glycosyl Sulfoxide Activation Process
  作者：Wei Chen、Pinru Wu、Jing Zeng、Jing Fang、Zhiwen Liao、Lei Cai、Hao Wang、Lingkui Meng、Qian Wan

  DOI：10.1002/cjoc.202200706

  日期：2023.2.15

  an extensive series of studies, the precise mechanism of this powerful glycosylation is still not fully understood. To address these 30-year puzzles, the far side of Kahne glycosylation is explored in this study. After a series of control and tracking experiments, a number of important intermediates including glycosyl oxo-sulfonium ion and sulfenic anhydride (Crich's intermediate) are suggested to be

  Kahne 糖基化的发现使碳水化合物化学向前迈进了一大步。尽管进行了一系列广泛的研究，但这种强大的糖基化作用的确切机制仍未完全了解。为了解决这些 30 年的难题，本研究探索了 Kahne 糖基化的另一面。经过一系列的控制和跟踪实验，一些重要的中间体包括糖基氧代硫离子和亚磺酸酐（Crich 中间体）被认为是复杂反应途径的原因。它还表明，除了传统的离子糖基化途径外，一种新的自由基途径很可能有助于产生各种副产物和副产物。这项研究提供了对 Kahne 糖基化的进一步了解，