1,5-anhydro-2-deoxy-1,2-C-(exo-acetoxymethylmethylene)-3,4,6-tri-O-benzyl-α-D-glucitol | 1361033-36-4

• 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: 1,5-anhydro-2-deoxy-1,2-C-(exo-acetoxymethylmethylene)-3,4,6-tri-O-benzyl-α-D-glucitol
• 英文别名: [(1R,3R,4S,5R,6S,7R)-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptan-7-yl]methyl acetate
• CAS: 1361033-36-4
• 化学式: C₃₁H₃₄O₆
• 分子量: 502.607
• InChiKey: XBKOSAVGKNWXHR-MDDVVAPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-deoxy-1,2-C-(exo-acetoxymethylmethylene)-3,4,6-tri-O-benzyl-α-D-glucitol 在 aluminium(III) triflate 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到(2R,5S)-5-(benzyloxy)-6-(benzyloxymethyl)-2-methyl-5,6-dihydro-2H-pyran-3-carbaldehyde
  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：

  3,4,6-三苄氧基-D-葡萄烯糖 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 1,5-anhydro-2-deoxy-1,2-C-(exo-acetoxymethylmethylene)-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