(2R,3S,4S,5S)-2,3,4-Tri-O-benzylhexane-1,2,3,4,5,6-hexol | 140386-68-1

• 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: (2R,3S,4S,5S)-2,3,4-Tri-O-benzylhexane-1,2,3,4,5,6-hexol
• 英文别名: (2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)hexane-1,2,6-triol
• CAS: 140386-68-1
• 化学式: C₂₇H₃₂O₆
• 分子量: 452.547
• InChiKey: VEVLEKXTJKDJAO-XUJYPJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S)-2,3,4-Tri-O-benzylhexane-1,2,3,4,5,6-hexol 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以93%的产率得到L-山梨糖醇
  参考文献：
  名称：

  Stereocontrolled total synthesis of the unnatural enantiomers of castanospermine and 1-epi-castanospermine

  摘要：

  A concise practical synthesis (13 steps, ca. 10-12% overall yield) of the unnatural enantiomer of castanospermine ((-)-1) and its 1-epimer 2 from 2,3,4-tri-O-benzyl-D-xylose (3) is described. Key steps in the synthesis are two organometal aldehyde additions, vinylation of 3 to 4 and allylation of 6a to 11, both of which proceed with a considerably high degree of stereocontrol. The fused ring system is generated from the acyclic amino polyol derivative 16a by two successive S(N)2-type cyclizations. Notably, the annulation of the six-membered ring makes use of tetravalent phosphonium reagents (Appel or Mitsunobu type) which cyclize the amino alcohol 22a/b directly to 23a/b without need for N-deprotection and O-activation manipulations.

  DOI：

  10.1021/jo00037a043
• 作为产物：
  描述：

  (2S,3S,4R,5S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)hexane-1,2,3,4,5,6-hexol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到(2R,3S,4S,5S)-2,3,4-Tri-O-benzylhexane-1,2,3,4,5,6-hexol
  参考文献：
  名称：

  Stereocontrolled total synthesis of the unnatural enantiomers of castanospermine and 1-epi-castanospermine

  摘要：

  A concise practical synthesis (13 steps, ca. 10-12% overall yield) of the unnatural enantiomer of castanospermine ((-)-1) and its 1-epimer 2 from 2,3,4-tri-O-benzyl-D-xylose (3) is described. Key steps in the synthesis are two organometal aldehyde additions, vinylation of 3 to 4 and allylation of 6a to 11, both of which proceed with a considerably high degree of stereocontrol. The fused ring system is generated from the acyclic amino polyol derivative 16a by two successive S(N)2-type cyclizations. Notably, the annulation of the six-membered ring makes use of tetravalent phosphonium reagents (Appel or Mitsunobu type) which cyclize the amino alcohol 22a/b directly to 23a/b without need for N-deprotection and O-activation manipulations.

  DOI：

  10.1021/jo00037a043