(-)-(4S,5R,6S,7S)-4,5,6,7,8-pentakis-benzyloxy-2-methylidene-octanenitrile | 681826-48-2

• 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: (-)-(4S,5R,6S,7S)-4,5,6,7,8-pentakis-benzyloxy-2-methylidene-octanenitrile
• CAS: 681826-48-2
• 化学式: C₄₄H₄₅NO₅
• 分子量: 667.845
• InChiKey: UYXORFPGVBAWSG-IYTFMMMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.01
• 重原子数：
  50.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.94
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (-)-(4S,5R,6S,7S)-4,5,6,7,8-pentakis-benzyloxy-2-methylidene-octanenitrile 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇 为溶剂， 反应 216.0h， 生成 (-)-(4S,5R,6S,7S)-4,5,6,7,8-pentakis-benzyloxy-2-methylidene-octanoic acid
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069
• 作为产物：
  描述：

  溴甲苯 、 (-)-(4S,5R,6S,7S)-4,5,6,7,8-pentahydroxy-2-methylidene-octanenitrile 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以58%的产率得到(-)-(4S,5R,6S,7S)-4,5,6,7,8-pentakis-benzyloxy-2-methylidene-octanenitrile
  参考文献：
  名称：

  Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues

  摘要：

  A new approach to the synthesis of ulosonic acids KDO and DAH is described. The key step is the C-5-C-6 bond formation catalysed by fructose-1,6-bisphosphate aldolase (for KDO) or transketolase (for DAH) using substituted acrylonitrile alpha-hydroxyaldehyde. All asymmetric carbon configurations are determined in an enzymatic step by the means of deshydrogenase or lipase. This strategy, using a non-metabolism pathway, allows access to novel precursors of KDO, DAH and analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.069