(2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol | 140201-56-5

• 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: (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol
• CAS: 140201-56-5
• 化学式: C₃₄H₄₄O₈
• 分子量: 580.719
• InChiKey: OPUTXZAWYPOYJC-NKDGLFHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  42.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  84.84
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-1,2,3,4,5,6-hexol 在 sodium hydride 、 臭氧 、 三苯基膦 作用下， 反应 24.0h， 生成 (3R,4R,5R,6S,7R)-3,5,6,7-Tetrakis-benzyloxy-4,8-bis-methoxymethoxy-octanal
  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,3R,4S,5R)-3,4,5-Tris(benzyloxy)-2,6-bis(methoxymethoxy)hexanal 、 3-溴丙烯 在 chromium chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以9%的产率得到(2R,3S,4R,5R,6S)-2,3,4-Tri-O-benzyl-1,5-bis-O-(methoxymethyl)-8-nonene-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