1,5-anhydro-2-deoxy-1,2-C-exo-(2'-acetoxyhexylidene)-3,4,6-tri-O-benzyl-α-D-glucitol | 1361033-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2-deoxy-1,2-C-exo-(2'-acetoxyhexylidene)-3,4,6-tri-O-benzyl-α-D-glucitol
• CAS: 1361033-44-4
• 化学式: C₃₅H₄₂O₆
• 分子量: 558.715
• InChiKey: OMRSJVYWSDSPOD-YQUCPMTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-deoxy-1,2-C-exo-(2'-acetoxyhexylidene)-3,4,6-tri-O-benzyl-α-D-glucitol 、 苯甲醇 在 aluminium(III) triflate 作用下， 以 乙腈 为溶剂， 生成 benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(Z)-1'-hexenyl]-α-D-glucopyranoside 、 benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(E)-1'-hexenyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Extending the scope of the Ferrier reaction: fragmentation-rearrangement reactions of selectively substituted 1,2-cyclopropanated glucose derivatives

  摘要：

  Two further variations of the Ferrier-type allylic rearrangements of 1,2-cyclopropanated glucose derivatives bearing an acetoxylated carbon at the 1'-position are described. In the first, treatment of the cyclopropanated sugar with a nucleophile (ROH, PhSH, azide) and Lewis acid (BF3 center dot Et2O or Al(OTf)(3)), gives 2-C-vinyl glucosides in good yields and alpha-selectivities. Alternatively, treatment with a combination of Lewis acid and acetic acid leads to a novel fragmentation-rearrangement to form a 2,3-dehydro-2-formyl-C-glycoside.[GRAPHICS](C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.006
• 作为产物：
  描述：

  、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以44 mg的产率得到1,5-anhydro-2-deoxy-1,2-C-exo-(2'-acetoxyhexylidene)-3,4,6-tri-O-benzyl-α-D-glucitol
  参考文献：
  名称：

  Extending the scope of the Ferrier reaction: fragmentation-rearrangement reactions of selectively substituted 1,2-cyclopropanated glucose derivatives

  摘要：

  Two further variations of the Ferrier-type allylic rearrangements of 1,2-cyclopropanated glucose derivatives bearing an acetoxylated carbon at the 1'-position are described. In the first, treatment of the cyclopropanated sugar with a nucleophile (ROH, PhSH, azide) and Lewis acid (BF3 center dot Et2O or Al(OTf)(3)), gives 2-C-vinyl glucosides in good yields and alpha-selectivities. Alternatively, treatment with a combination of Lewis acid and acetic acid leads to a novel fragmentation-rearrangement to form a 2,3-dehydro-2-formyl-C-glycoside.[GRAPHICS](C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.006