(2R,4R)-3-azido-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate) | 620948-24-5

• 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: (2R,4R)-3-azido-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate)
• 英文别名: [(2R,4R)-3-azido-2,4-dihydroxy-5-[2,4,6-tri(propan-2-yl)phenyl]sulfonyloxypentyl] 2,4,6-tri(propan-2-yl)benzenesulfonate
• CAS: 620948-24-5
• 化学式: C₃₅H₅₅N₃O₈S₂
• 分子量: 709.969
• InChiKey: ZMMNKQWNZNWREV-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,4R)-3-azido-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate) 在 sodium hydride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.0h， 以71%的产率得到(2R,4R)-3-azido-1,2:4,5-diepoxypentane
  参考文献：
  名称：

  Short Synthesis of Enantiopure C₂-Symmetric 1,2:4,5-Diepoxypentane and “Pseudo”-C₂-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol

  摘要：

  On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.

  DOI：

  10.1021/jo034374x
• 作为产物：
  描述：

  (2S,4S)-1,2:4,5-di-O-(3,3-pentylidene)arabitol 在 吡啶 、 sodium azide 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (2R,4R)-3-azido-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate)
  参考文献：
  名称：

  Short Synthesis of Enantiopure C₂-Symmetric 1,2:4,5-Diepoxypentane and “Pseudo”-C₂-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol

  摘要：

  On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.

  DOI：

  10.1021/jo034374x

文献信息

• Short Synthesis of Enantiopure <i>C</i>₂-Symmetric 1,2:4,5-Diepoxypentane and “<i>Pseudo</i>”-<i>C</i>₂-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol
  作者：A. James Boydell、Martin J. Jeffery、Eva Bürkstümmer、Bruno Linclau

  DOI：10.1021/jo034374x

  日期：2003.10.1

  On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C-2-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C-2-symmetrical 1,2:4,5-bis-epoxypentane building block I is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.