(3aR,5R,6S,6aR)-1-benzyl-5-(hydroxymethyl)-5-phenylmethoxy-3a,4,6,6a-tetrahydro-3H-cyclopenta[c][1,2]oxazol-6-ol | 197702-02-6

• 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: (3aR,5R,6S,6aR)-1-benzyl-5-(hydroxymethyl)-5-phenylmethoxy-3a,4,6,6a-tetrahydro-3H-cyclopenta[c][1,2]oxazol-6-ol
• CAS: 197702-02-6
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: JNZZONXIJURMPY-JSXRDJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-1-benzyl-5-(hydroxymethyl)-5-phenylmethoxy-3a,4,6,6a-tetrahydro-3H-cyclopenta[c][1,2]oxazol-6-ol 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 环己烯 、 正丁醇 为溶剂， 生成 (1'R,2'S,3'R,4'R)-9-<1,4-bis(hydroxymethyl)-1,2-dihydroxycyclopent-3-yl>-6-dimethylaminoadenine
  参考文献：
  名称：

  Chiral Carbocyclic Nucleosides from d-Glucose:  Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings

  摘要：

  Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at C-5 or C-l and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated aminocarbocycles which were subsequently used as the precursors for carbocyclic nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction. An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred spontaneously under mild condition, though similar reactions are reported to occur at higher temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy substituent in the carbocycle seems to play a crucial role in this reaction.

  DOI：

  10.1021/jo981955r
• 作为产物：
  描述：

  (1R)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 在 sodium tetrahydroborate 、 sodium periodate 、 硫酸 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 39.0h， 生成 (3aR,5R,6S,6aR)-1-benzyl-5-(hydroxymethyl)-5-phenylmethoxy-3a,4,6,6a-tetrahydro-3H-cyclopenta[c][1,2]oxazol-6-ol
  参考文献：
  名称：

  Application of Intramolecular Nitrone Cycloaddition Reaction:  Synthesis of Chiral Aminocarbocycles and Carbocyclic Nucleosides from Carbohydrate Precursors

  摘要：

  DOI：

  10.1021/jo971342z