(2S,3S,4R)-2-azido-3,4-bis(trimethylsilyloxy)octadecan-1-ol | 1443504-02-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3S,4R)-2-azido-3,4-bis(trimethylsilyloxy)octadecan-1-ol
• CAS: 1443504-02-6
• 化学式: C₂₄H₅₃N₃O₃Si₂
• 分子量: 487.874
• InChiKey: YJUKIRYUEWHISH-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.19
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-azido-3,4-bis(trimethylsilyloxy)octadecan-1-ol 、 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide 在 四丁基碘化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以79%的产率得到
  参考文献：
  名称：

  使用过-O-三甲基甲硅烷基-糖基碘化物作为糖基供体的寡糖合成。

  摘要：

  已发现三甲基甲硅烷基（TMS）保护基对于寡糖合成中糖基供体和受体底物的同时保护非常有用。因此，尽管全-O-三甲基甲硅烷基化的糖基碘化物用作糖基供体，但发现那些带有选择性暴露的伯羟基的基团适合作为反应的糖基受体。发现便宜且可商购的三烷基胺，三乙胺是糖基化的有效促进剂。重要的是，该反应是α-立体特异性的，并且产物的产率为58％-78％。

  DOI：

  10.1016/j.carres.2016.03.019
• 作为产物：
  描述：

  (2S,3S,4R)-2-叠氮基-1,3,4-十八烷三醇 在 吡啶 、 ammonium acetate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,3S,4R)-2-azido-3,4-bis(trimethylsilyloxy)octadecan-1-ol
  参考文献：
  名称：

  Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate

  摘要：

  A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.039

文献信息

• Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor
  作者：Hong Wang、Yanli Cui、Rong Zou、Zhaodong Cheng、Weirong Yao、Yangyi Mao、Yongmin Zhang

  DOI：10.1016/j.carres.2016.03.019

  日期：2016.6

  been found to be very useful for the simultaneous protection of both the glycosyl donor- and the acceptor-substrates in oligosaccharide synthesis. Thus, while the per-O-trimethylsilylated glycosyl iodides served as the glycosyl donor, those bearing selectively exposed primary hydroxyl groups were found suitable as the glycosyl acceptor for the reaction. The cheap and commercially available trialkylamine

  已发现三甲基甲硅烷基（TMS）保护基对于寡糖合成中糖基供体和受体底物的同时保护非常有用。因此，尽管全-O-三甲基甲硅烷基化的糖基碘化物用作糖基供体，但发现那些带有选择性暴露的伯羟基的基团适合作为反应的糖基受体。发现便宜且可商购的三烷基胺，三乙胺是糖基化的有效促进剂。重要的是，该反应是α-立体特异性的，并且产物的产率为58％-78％。
• Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate
  作者：Yanli Cui、Zhaodong Cheng、Jianwei Mao、Yongping Yu

  DOI：10.1016/j.tetlet.2013.05.039

  日期：2013.7

  A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine. (C) 2013 Elsevier Ltd. All rights reserved.