(Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-hept-5-en-1-ol | 636586-60-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-hept-5-en-1-ol
• CAS: 636586-60-2
• 化学式: C₂₈H₃₂O₄
• 分子量: 432.56
• InChiKey: SYYDSOVQOULNDI-JABONMPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-hept-5-en-1-ol 在 氯化亚砜 、 sodium acetate 、 四丁基碘化铵 、 sodium hydride 、 臭氧 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.25h， 生成 (2S,3R,4R,5R)-2,3,4,5,9-Pentakis-benzyloxy-nonanal
  参考文献：
  名称：

  Universal NMR Databases for Contiguous Polyols

  摘要：

  On the basis of 1,2,3-triols 1asimilar tod, 1,2,3,4-tetraols 2asimilar toh, and 1,2,3,4,5-pentaols 3asimilar top, NMR databases with four types of profile-descriptors (C-13-, H-1-, and H-1(OH)-chemical shifts and vicinal spin-coupling constants) for contiguous polyols are reported. To systematically assess the relative values of these databases, a case study has been conducted on heptaols 4asimilar tod, through which the gamma- and delta-effects have been recognized to refine the C-13 and H-1 chemical shift profile predicted via an application of the concept of self-contained nature. The magnitudes of gamma- and delta-effects depend on a specific stereochemical arrangement of the functional groups present in both the inside and outside of a self-contained box and are significant only for the stereoisomers belonging to a specific sub-group. With the exception of the stereochemical arrangement of functional groups belonging to a specific sub-group, the gamma- and delta-effects can, at the first order of approximation, be ignored for the stereochemical analysis of unknown compounds. For the stereoisomers belonging to a specific sub-group, it is necessary to refine, with incorporation of the gamma- and delta-effects, the profile predicted at the first order of approximation. With use of heptaols 4asimilar tod, the values of (3)J(H,H) profiles have been assessed. Two methods, one using profiles consisting of three contiguous (3)J(H,H) constants and the other using profiles consisting of two contiguous (3)J(H,H) constants, have been developed. A stereochemical analysis based on three, or two, contiguous (3)J(H,H) profiles is operationally simpler than one based on C-13 and H-1 chemical shift profiles. Therefore, it is recommended to use a (3)J(H,H) profile as the primary device to predict the stereochemistry of unknown polyols and C-13 and H-1 chemical shift profiles as the secondary devices to confirm the predicted stereochemistry.

  DOI：

  10.1021/ja0375481
• 作为产物：
  描述：

  碘化乙基三苯基瞵 、 2,3,4-tri-O-benzyl-D-arabinopyranose 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 以57%的产率得到(Z)-(2R,3S,4R)-2,3,4-Tris-benzyloxy-hept-5-en-1-ol
  参考文献：
  名称：

  Universal NMR Databases for Contiguous Polyols

  摘要：

  On the basis of 1,2,3-triols 1asimilar tod, 1,2,3,4-tetraols 2asimilar toh, and 1,2,3,4,5-pentaols 3asimilar top, NMR databases with four types of profile-descriptors (C-13-, H-1-, and H-1(OH)-chemical shifts and vicinal spin-coupling constants) for contiguous polyols are reported. To systematically assess the relative values of these databases, a case study has been conducted on heptaols 4asimilar tod, through which the gamma- and delta-effects have been recognized to refine the C-13 and H-1 chemical shift profile predicted via an application of the concept of self-contained nature. The magnitudes of gamma- and delta-effects depend on a specific stereochemical arrangement of the functional groups present in both the inside and outside of a self-contained box and are significant only for the stereoisomers belonging to a specific sub-group. With the exception of the stereochemical arrangement of functional groups belonging to a specific sub-group, the gamma- and delta-effects can, at the first order of approximation, be ignored for the stereochemical analysis of unknown compounds. For the stereoisomers belonging to a specific sub-group, it is necessary to refine, with incorporation of the gamma- and delta-effects, the profile predicted at the first order of approximation. With use of heptaols 4asimilar tod, the values of (3)J(H,H) profiles have been assessed. Two methods, one using profiles consisting of three contiguous (3)J(H,H) constants and the other using profiles consisting of two contiguous (3)J(H,H) constants, have been developed. A stereochemical analysis based on three, or two, contiguous (3)J(H,H) profiles is operationally simpler than one based on C-13 and H-1 chemical shift profiles. Therefore, it is recommended to use a (3)J(H,H) profile as the primary device to predict the stereochemistry of unknown polyols and C-13 and H-1 chemical shift profiles as the secondary devices to confirm the predicted stereochemistry.

  DOI：

  10.1021/ja0375481