2,3,4-tri-O-benzyl-5-epi-cyclophellitol | 956470-42-1

• 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: 2,3,4-tri-O-benzyl-5-epi-cyclophellitol
• 英文别名: [(1R,2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-7-oxabicyclo[4.1.0]heptan-2-yl]methanol
• CAS: 956470-42-1
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: PIBHUJIDJZGWDM-BUNJHDQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-5-epi-cyclophellitol 在 三氯化硼 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 以98%的产率得到(1S,2R,3S,4R,5S,6R)-5-hydroxymethyl-7-oxabicyclo[4.1.0]heptane-2,3,4-triol
  参考文献：
  名称：

  An unexpected access to 5-epi-cyclophellitol: a new cyclitol member

  摘要：

  A thorough reinvestigation of the hydroboration-oxidation of methylene epoxycyclohexane 3 has revealed the formation of a direct precursor of the hitherto unreported 5-epi-cyclophellitol. Hydroboration of the starting precursor 3 takes place with total and opposite stereocontrol to that previously described in the literature. The sterochemistry of this new cyclophellitol isomer has been unambiguously confirmed by comparison with reference compounds obtained by independent methods. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.002
• 作为产物：
  描述：

  (1R,2R,3S,4R,6R)-2,3,4-Tris-benzyloxy-5-methylene-7-oxa-bicyclo[4.1.0]heptane 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 以72%的产率得到2,3,4-tri-O-benzyl-5-epi-cyclophellitol
  参考文献：
  名称：

  An unexpected access to 5-epi-cyclophellitol: a new cyclitol member

  摘要：

  A thorough reinvestigation of the hydroboration-oxidation of methylene epoxycyclohexane 3 has revealed the formation of a direct precursor of the hitherto unreported 5-epi-cyclophellitol. Hydroboration of the starting precursor 3 takes place with total and opposite stereocontrol to that previously described in the literature. The sterochemistry of this new cyclophellitol isomer has been unambiguously confirmed by comparison with reference compounds obtained by independent methods. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.002

文献信息

• Corrigendum to “An unexpected access to 5-epi-cyclophellitol, a new cyclitol member” [Tetrahedron: Asymmetry 18/16 (2007) 1971]
  作者：Pedro Serrano、Meritxell Egido-Gabás、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/j.tetasy.2009.04.011

  日期：2009.5