(2R,4R)-pentane-1,2,4,5-tetraol | 41107-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-pentane-1,2,4,5-tetraol
• 英文别名: (-)-pentanetetrol；L-threo-3-deoxy-pentitol；L-3-deoxy-arabinitol；3-Desoxy-L-threo-pentit；(2R,4R)-pentane-1,2,4,5-tetrol
• CAS: 41107-44-2
• 化学式: C₅H₁₂O₄
• 分子量: 136.148
• InChiKey: VHDMXHLHMMROPO-RFZPGFLSSA-N

物化性质

• 熔点：
  104-106 °C(Solv: ethanol (64-17-5); hexane (110-54-3))
• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-pentane-1,2,4,5-tetraol 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (+)-(2R,2'R)-methylenebis(oxirane)
  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 、 硫酸 、 三乙基硼氢化锂 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (2R,4R)-pentane-1,2,4,5-tetraol
  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

• Stereochemical correlation of di- and trihydroxy-.BETA.-diketone fungal metabolites, (-)-terredionol and terremutin hydrate, with sugar alcohols: The absolute configuration of (-)-terredionol.
  作者：YOSHISUKE TSUDA、TETSUJI NUNOZAWA、KEIICHI NITTA、YUZURU YAMAMOTO

  DOI：10.1248/cpb.28.920

  日期：——

  The structures, including stereochemistries, of two fungal metabolites, terremutin hydrate and (-)-terredionol, were shown to be [4R, 5s, 6S]-4, 5, 6-trihydroxy-2-methylcyclohexane-1, 3-dione (III) and [4R, 6R]-(-)-4, 6-dihydroxy-2-methylcyclohexane-1, 3-dione (IV) by correlating them with xylitol and [2R, 4R]-(-)-pentane-1, 2, 4, 5-tetrol, respectively.

  通过将两种真菌代谢物--水合特瑞木汀和 (-)-terredionol 与 x 轴相关联，证明了它们的结构（包括立体化学结构）分别为 [4R，5s，6S]-4，5，6-三羟基-2-甲基环己烷-1，3-二酮 (III) 和 [4R，6R]-(-)-4，6-二羟基-2-甲基环己烷-1，3-二酮 (IV) 、3-二酮 (III) 和 [4R，6R]-(-)-4，6-二羟基-2-甲基环己烷-1，3-二酮 (IV)，并将它们与木糖醇和 [2R，4R]-(-)-戊烷-1，2，4，5-四醇联系起来。
• Zinner,H.; Reck,R., Journal fuer Praktische Chemie (Leipzig), 1973, vol. 315, p. 137 - 143
  作者：Zinner,H.、Reck,R.

  DOI：——

  日期：——
• 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.