(2S,3S,4R,5R,6S)-2-iodo-6-methyl-3,4,5-tris(phenylmethoxy)oxane | 250691-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4R,5R,6S)-2-iodo-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• CAS: 250691-61-3
• 化学式: C₂₇H₂₉IO₄
• 分子量: 544.429
• InChiKey: GDFOZYIOBGXYQL-RBGCBHJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S)-2-iodo-6-methyl-3,4,5-tris(phenylmethoxy)oxane 在 四丁基碘化铵 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 2,3,4-tri-O-benzyl-α-L-fucopyranosyl azide
  参考文献：
  名称：

  糖基叠氮化物与三芳基膦的无痕Staudinger连接：糖基酰胺的立体选择性合成†

  摘要：

  α-糖基酰胺可通过无痕施陶丁格与二苯基膦酰基-苯基酯的连接由相应的O-苄基-α-糖基叠氮化物合成4。所用的所有膦及其苯酚前体在4°C的空气中均可保持稳定数月。还原中间体的快速分子内捕集导致酰胺键的直接形成，继而防止了差向异构化并允许在异头碳上保留构型。当反应在极性非质子溶剂中进行时，产率和α-选择性高。苄基醚保护基的去除是通过催化氢化来实现的。α-糖基酰胺代表了一类实际上未开发的不可水解的单糖衍生物，可以作为糖模拟物找到有用的应用。NMR光谱的构象研究证实，葡萄糖，半乳糖和fuco系列中的脱保护α-糖基酰胺保留了单糖的正常吡喃糖构象。膦的反应4用四ø -乙酰基葡糖基叠氮化物是nonstereoconservative，并在良好的产率，并与来自两个α和β叠氮化物开始完整的立体选择性获得β糖基酰胺。

  DOI：

  10.1021/jo060409s
• 作为产物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R,6S)-2-iodo-6-methyl-3,4,5-tris(phenylmethoxy)oxane
  参考文献：
  名称：

  Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

  摘要：

  alpha-Glycosyl azides can be transformed into the corresponding alpha-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The of alpha-acetamides of per-O-benzylated-fucose, per-O-benzylated-glucose and per-O-benzylated-galactose were selectively synthesized by this process. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.159

文献信息

• Glycosyl iodides are highly efficient donors under neutral conditions
  作者：Michael J. Hadd、Jacquelyn Gervay

  DOI：10.1016/s0008-6215(99)00146-9

  日期：1999.7

  Abstract Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature

  摘要制备了糖基碘化物并在中性条件下进行糖基化。该反应是高效的，即使具有空间上要求的糖基受体也能得到α糖苷。葡萄糖基碘与烯丙醇的反应最慢，需要回流条件。半乳糖基碘化物是反应性的中间产物，在室温下3小时内可提供烯丙基糖苷，而岩藻糖基碘化物的糖基化在相似条件下可在不到1小时内发生。用包括异头羟基在内的各种受体证明了反应的范围和局限性，得到了海藻糖类似物。在不存在C-2参与的情况下，只需将溶剂从苯改成乙腈就可以实现葡萄糖基碘化物的β-选择性糖基化。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of α-Glycosyl Phosphites and Phosphoramidites via <i>O</i>-Selective Glycosylation of <i>H</i>-Phosphonate Derivatives
  作者：Fumiko Matsumura、Natsuhisa Oka、Takeshi Wada

  DOI：10.1021/ol802190x

  日期：2008.11.20

  A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various alpha-glycosyl phosphites; and phosphoramidites in a highly stereoselective manner with complete O-selectivity.