1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose
• 英文别名: 2,3,4-tri-O-allyl-1,6-anhydro-β-D-glucopyranose；O-allylated 1,6-anhydro-beta-D-glucopyranose；(1R,2R,3S,4R,5R)-2,3,4-tris(prop-2-enoxy)-6,8-dioxabicyclo[3.2.1]octane
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: CGPOORDXQRSNCP-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 作用下， 以78%的产率得到2,3,4,-tri-O-allyl-1-thio-α-D-glucopyranose
  参考文献：
  名称：

  A direct and stereospecific approach to the synthesis of α-glycosyl thiols

  摘要：

  本文介绍了一种合成δ-糖基硫醇的新的简单方法。在催化剂 TMSOTf 的作用下，1,6-酸酐糖与市售的双(三甲基硅)硫化物开环，以非常高的产率和立体特异性的方式顺利得到了δ-糖基硫醇。

  DOI：

  10.1039/b804536d
• 作为产物：
  描述：

  3-溴丙烯 、 1,6-脱水-β-D-葡萄糖 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.0h， 以95%的产率得到1,6-anhydro-2,3,4-tri-O-allyl-β-D-glucopyranose
  参考文献：
  名称：

  一锅，高立体选择性合成二硫缩醛-α，α-二糖苷。

  摘要：

  据报道一步接触二硫缩醛-α，α-二糖苷。合成策略基于通过双（三甲基甲硅烷基）硫化物对1,6脱水糖的高度立体选择性开环，对醛或酮进行硫代缩醛化反应。

  DOI：

  10.3390/molecules23040914

文献信息

• Stereoselective synthesis of α-glycosyl azides by ring-opening of 1,6-anhydrosugars with trimethylsilyl azide
  作者：Tianyu Cui、Raymond Smith、Xiangming Zhu

  DOI：10.1016/j.carres.2015.08.002

  日期：2015.10

  We describe here an expedient and highly stereoselective procedure for the synthesis of alpha-glycosyl azides. Treatment of 1,6-anhydrosugars with trimethylsilyl azide in the presence of trimethylsilyl triflate led to the formation of alpha-glycosyl azides. All the reactions were highly stereoselective and afforded the alpha-glycosyl azides in good to excellent yields.

  我们在这里描述了一种方便且高度立体选择性的合成α-糖基叠氮化物的方法。在三甲基甲硅烷基三氟甲磺酸酯存在下用三甲基甲硅烷基叠氮化物处理1，6-脱水糖导致形成α-糖基叠氮化物。所有反应都是高度立体选择性的，并以良好至优异的产率提供了α-糖基叠氮化物。
• Synthesis of substituted titanocene dichloride derivatives by hydrosilylation
  作者：Tomáš Strašák、Jindřich Karban、Lucie Červenková Št'astná、Lucie Maixnerová、Anna Březinová、Martin Bernard、Radek Fajgar

  DOI：10.1016/j.jorganchem.2014.06.009

  日期：2014.10

  Substituted titanocene complexes have been prepared by hydrosilylation of organic substrates containing a terminal double bond by cyclopentadienyl complexes of titanium bearing a Si–H functional group. This new synthetic protocol is demonstrated by synthesis of mono-, bi- and trihomonuclear complexes. The structures of prepared compounds have been characterized by standard methods (NMR, IR, and HRMS).

  取代的钛茂配合物是通过将带有末端双键的有机底物通过带有Si-H官能团的钛的环戊二烯基配合物氢化硅烷化而制备的。单，双和三核复合物的合成证明了这种新的合成方案。制备的化合物的结构已通过标准方法（NMR，IR和HRMS）进行了表征。
• Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS
  申请人：Zhu Xiangming

  公开号：US20100184711A1

  公开（公告）日：2010-07-22

  The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.

  本发明涉及用于制备α-糖基硫醇和α-S-链接糖基酰胺的立体选择性方法。
• Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars
  作者：Xiangming Zhu、Ravindra T. Dere、Junyan Jiang、Lei Zhang、Xiaoxia Wang

  DOI：10.1021/jo202069y

  日期：2011.12.16

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.