[(2R,3R,4R,5S)-3,5-bis[[ethyl(dimethyl)silyl]oxy]-2-[[ethyl(dimethyl)silyl]oxymethyl]oxan-4-yl]oxy-ethyl-dimethylsilane | 1418118-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5S)-3,5-bis[[ethyl(dimethyl)silyl]oxy]-2-[[ethyl(dimethyl)silyl]oxymethyl]oxan-4-yl]oxy-ethyl-dimethylsilane
• CAS: 1418118-67-8
• 化学式: C₂₂H₅₂O₅Si₄
• 分子量: 508.994
• InChiKey: AGVLUNFFUKLARV-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  [(2R,3R,4R,5S)-3,5-bis[[ethyl(dimethyl)silyl]oxy]-2-[[ethyl(dimethyl)silyl]oxymethyl]oxan-4-yl]oxy-ethyl-dimethylsilane 在 二乙基硅烷 、 [(2,6-[OP(tBu)2]2C₆H₃)Ir(H)(acetone)]⁺[B(C₆F₅)4]^- 作用下， 反应 336.0h， 以17%的产率得到正己烷
  参考文献：
  名称：

  Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s)

  摘要：

  In light of diminishing petroleum feed-stocks, there is significant interest in developing carbohydrate defunctionalization reactions. In this context we have examined the use of iridium pincer catalysts for the hydrosilylative reduction of sugars, and we report herein complete reduction of silyl-protected glucose to a mixture of hexane isomers.

  DOI：

  10.1021/ja3110494
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 吡啶 、 二甲基乙基硅烷 、 [(2,6-[OP(tBu)2]2C₆H₃)Ir(H)(acetone)]⁺[B(C₆F₅)4]^- 作用下， 反应 48.33h， 生成 [(2R,3R,4R,5S)-3,5-bis[[ethyl(dimethyl)silyl]oxy]-2-[[ethyl(dimethyl)silyl]oxymethyl]oxan-4-yl]oxy-ethyl-dimethylsilane
  参考文献：
  名称：

  Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s)

  摘要：

  In light of diminishing petroleum feed-stocks, there is significant interest in developing carbohydrate defunctionalization reactions. In this context we have examined the use of iridium pincer catalysts for the hydrosilylative reduction of sugars, and we report herein complete reduction of silyl-protected glucose to a mixture of hexane isomers.

  DOI：

  10.1021/ja3110494

文献信息

• Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s)
  作者：Matthew P. McLaughlin、Laura L. Adduci、Jennifer J. Becker、Michel R. Gagné

  DOI：10.1021/ja3110494

  日期：2013.1.30

  In light of diminishing petroleum feed-stocks, there is significant interest in developing carbohydrate defunctionalization reactions. In this context we have examined the use of iridium pincer catalysts for the hydrosilylative reduction of sugars, and we report herein complete reduction of silyl-protected glucose to a mixture of hexane isomers.