6-deoxy-1,4:2,5-di-anhydro-3-O-benzyl-L-gulitol | 1138337-95-7

• 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: 6-deoxy-1,4:2,5-di-anhydro-3-O-benzyl-L-gulitol
• 英文别名: (1R,3S,4R,7R)-3-methyl-7-phenylmethoxy-2,5-dioxabicyclo[2.2.1]heptane
• CAS: 1138337-95-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: APDFMPHVGRODTK-WKSBVSIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-deoxy-1,4:2,5-di-anhydro-3-O-benzyl-L-gulitol 在 盐酸 、 三甲基氯硅烷 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以76%的产率得到(2S,3R,4S,5S)-4-benzyloxy-5-iodomethyl-2-methyltetrahydrofuran-3-ol
  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：

  (2S,3R,4S)-4-O-benzylhex-5-ene-2,3,4-triol 在 sodium acetate 、 溶剂黄146 、 copper dichloride 、 palladium dichloride 作用下， 反应 12.0h， 以83%的产率得到6-deoxy-1,4:2,5-di-anhydro-3-O-benzyl-L-gulitol
  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

文献信息

• Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols
  作者：Miroslav Palík、Oľga Karlubíková、Daniela Lackovičová、Angelika Lásiková、Tibor Gracza

  DOI：10.1016/j.tet.2010.04.074

  日期：2010.7

  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.