4-O-benzyl-L-xylo-5-hexenitol | 1237530-35-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-O-benzyl-L-xylo-5-hexenitol
• 英文别名: (2S,3R,4R)-4-phenylmethoxyhex-5-ene-1,2,3-triol
• CAS: 1237530-35-6
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: UIKYNLPXVXZNDI-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-O-benzyl-L-xylo-5-hexenitol 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 10.0h， 生成
  参考文献：
  名称：

  Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols

  摘要：

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.074
• 作为产物：
  描述：

  4-O-benzyl-3-O-[(tert-butyl)-diphenylsilyl]-L-xylo-5-hexenitol 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以85%的产率得到4-O-benzyl-L-xylo-5-hexenitol
  参考文献：
  名称：

  Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols

  摘要：

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.074