(1,2,3/5)-3-hydroxymethyl-1,2,5-cyclohexanetriol | 74517-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,2,3/5)-3-hydroxymethyl-1,2,5-cyclohexanetriol
• 英文别名: (1R,2S,4R,6S)-6-(hydroxymethyl)cyclohexane-1,2,4-triol
• CAS: 74517-38-7；74560-69-3
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: CDEBXVUQBIUXBB-BNHYGAARSA-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

• 作为反应物：
  描述：

  三苯基氯甲烷 、 (1,2,3/5)-3-hydroxymethyl-1,2,5-cyclohexanetriol 在 吡啶 作用下， 以3.55 g的产率得到(1R,2S,4R,6S)-6-Trityloxymethyl-cyclohexane-1,2,4-triol
  参考文献：
  名称：

  Synthesis of carbocyclic analogues of 3-deoxy-d-manno-2-octulosonic acid and N-acetylneuraminic acid

  摘要：

  A carbocyclic analogue of N-acetylneuraminic acid was synthesised from the Diels-Alder endo-adduct of furan and acrylic acid, and its ammonium salt was subjected to bioassay. In addition, carbocyclic analogues of 3-deoxy-D-manno-2-octulosonic acid were synthesised in racemic form from the same synthetic intermediate.

  DOI：

  10.1016/0008-6215(94)00344-f
• 作为产物：
  描述：

  Acetic acid (1S,2R,4S,6R)-4-acetoxy-2-acetoxymethyl-6-hydroxy-cyclohexyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以1.83 g的产率得到(1,2,3/5)-3-hydroxymethyl-1,2,5-cyclohexanetriol
  参考文献：
  名称：

  Synthesis of carbocyclic analogues of 3-deoxy-d-manno-2-octulosonic acid and N-acetylneuraminic acid

  摘要：

  A carbocyclic analogue of N-acetylneuraminic acid was synthesised from the Diels-Alder endo-adduct of furan and acrylic acid, and its ammonium salt was subjected to bioassay. In addition, carbocyclic analogues of 3-deoxy-D-manno-2-octulosonic acid were synthesised in racemic form from the same synthetic intermediate.

  DOI：

  10.1016/0008-6215(94)00344-f

文献信息

• Pseudo-sugars. VI. Synthesis of Six Isomers of 5-Hydroxymethyl-1,2,3,4-cyclohexanetetrol (Pseudo-hexopyranose) and Their Derivatives
  作者：Seiichiro Ogawa、Masayasu Ara、Takashi Kondoh、Michio Saitoh、Reiko Masuda、Tatsushi Toyokuni、Tetsuo Suami

  DOI：10.1246/bcsj.53.1121

  日期：1980.4

  Six isomers of 5-hydroxymethyl-1,2,3,4-cyclohexanetetrol, including naturally occurring (1,2/3,4,5)-isomer, and their several derivatives were synthesized from the exo-2-substituted endo-3-acetoxy-endo-5-acetoxymethyl-7-oxabicyclo[2.2.1]heptane compounds.

  从外向-2-取代内向-3-乙酰氧基-内向-5-乙酰氧甲基-7-氧杂双环[2.2.1]庚烷化合物中合成了六种 5-羟甲基-1,2,3,4-环己烷四醇异构体（包括天然存在的 (1,2/3,4,5) -异构体）及其多种衍生物。