4-epi-Validatol | 160708-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-epi-Validatol
• 英文别名: (1R,2R,3R,4S)-4-(Hydroxymethyl)-1,2,3-cyclohexanetriol；(1R,2R,3R,4S)-4-(hydroxymethyl)cyclohexane-1,2,3-triol
• CAS: 160708-46-3
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: HSWSNXXNDSZDNQ-BDVNFPICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  (1R,2R,3R,4S)-2,3-Bis-benzyloxy-4-hydroxymethyl-5,5-bis-methylsulfanyl-cyclohexanol 在 镍 作用下， 以68%的产率得到4-epi-Validatol
  参考文献：
  名称：

  Bisepoxides as biselectrophiles in the silicon-induced domino synthesis of highly functionalized carbocycles

  摘要：

  The reaction of silylated thioacetals 2a, b with different bisepoxides 1, 4, 5 is investigated. The silicon-induced domino reaction opens a short route from D-mannitol to the highly functionalized carbocycles 7-10. Using this cascade, 4-epi-validatol (12) is synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00386-x

文献信息

• SYNTHESIS OF CARBASUGARS FROM NUCLEOPHILIC ADDITION—RING CLOSURE (NARC)—DERIVED CYCLOALKENES
  作者：Patrick Perlmutter、Mark Rose

  DOI：10.1081/car-120003734

  日期：2002.5.31

  A short, enantioselective synthesis of carbasugars 4a-carba-α- l-xylofuranose 15, 4- epi-validatol 16and their corresponding carboxylic acids 11and 12 is reported. These compounds were prepared via a four-step sequence of nucleophilic addition, ring closure (NARC), dihydroxylation and reduction.

  carbasugars图4a-卡巴-α-的简短，对映选择性合成升-xylofuranose 15，4-外延-validatol 16和它们相应的羧酸11和12进行报告。这些化合物是通过亲核加成，闭环（NARC），二羟基化和还原的四个步骤来制备的。
• From Sugars to Carbocycles. 3. Synthesis of Validatol and 4-epi-Validatol from Mannose and Glucose
  作者：Karsten Krohn、Guido Boerner、Stephan Gringard

  DOI：10.1021/jo00099a044

  日期：1994.10

  Validatol (4) and 4-epi-validatol (8) are synthesized from mannose and glucose, respectively. The key step in the synthesis of 4 is the base-induced intramolecular displacement reaction of the epoxy dithiane 14 to yield the six-membered carbocycle 15 exclusively.