(2R,5S)-5-(benzyloxy)-6-(benzyloxymethyl)-2-methyl-5,6-dihydro-2H-pyran-3-carbaldehyde

• 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,5S)-5-(benzyloxy)-6-(benzyloxymethyl)-2-methyl-5,6-dihydro-2H-pyran-3-carbaldehyde
• 英文别名: (2R,3S,6R)-6-methyl-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-5-carbaldehyde
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: BPGOYXLTXFVAMN-VOQZNFBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Cossy, Janine; Rakotoarisoa, Haja, Synlett, 2000, # 5, p. 734 - 736
  作者：Cossy, Janine、Rakotoarisoa, Haja

  DOI：——

  日期：——
• Extending the scope of the Ferrier reaction: fragmentation-rearrangement reactions of selectively substituted 1,2-cyclopropanated glucose derivatives
  作者：Muganza Munyololo、David W. Gammon、Ilka Mohrholz

  DOI：10.1016/j.carres.2012.01.006

  日期：2012.4

  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.