(2R,4R)-di-O-(3,3-pentylidene)-3-deoxy-3-azidoarabitol | 620948-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-di-O-(3,3-pentylidene)-3-deoxy-3-azidoarabitol
• 英文别名: (4R)-4-[azido-[(4R)-2,2-diethyl-1,3-dioxolan-4-yl]methyl]-2,2-diethyl-1,3-dioxolane
• CAS: 620948-20-1
• 化学式: C₁₅H₂₇N₃O₄
• 分子量: 313.397
• InChiKey: MRFUIMSXPBWGKT-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4R)-di-O-(3,3-pentylidene)-3-deoxy-3-azidoarabitol 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 20.5h， 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
• 作为产物：
  描述：

  (2S,4S)-1,2:4,5-di-O-(3,3-pentylidene)arabitol 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (2R,4R)-di-O-(3,3-pentylidene)-3-deoxy-3-azidoarabitol
  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.