(2R,3S,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-(prop-2-ynoxymethyl)-3,4-dihydro-2H-pyran | 1003194-59-9

• 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)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-(prop-2-ynoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 1003194-59-9
• 化学式: C₃₁H₃₂O₅
• 分子量: 484.592
• InChiKey: CWMXCTYRZQUUDC-JFHPUIQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-(prop-2-ynoxymethyl)-3,4-dihydro-2H-pyran 、 L-薄荷醇 在 gold(III) chloride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以60%的产率得到(2S,4R,5S,6R)-3-methylidene-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3

  摘要：

  C-2 Methylene glycosides were synthesized from C-2 propargyloxymethyl glycals in a stereoselective manner using a catalytic quantity of AuCl3. The Au-catalyzed reaction was explored using various aglycones. The current protocol enables the preparation of C-2 methylene glycosides, tolerates diverse functional groups and is fast, catalytic and mild. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.144
• 作为产物：
  描述：

  3-溴丙炔 、 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-arabino-hex-1-enitol 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到(2R,3S,4R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-(prop-2-ynoxymethyl)-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3

  摘要：

  C-2 Methylene glycosides were synthesized from C-2 propargyloxymethyl glycals in a stereoselective manner using a catalytic quantity of AuCl3. The Au-catalyzed reaction was explored using various aglycones. The current protocol enables the preparation of C-2 methylene glycosides, tolerates diverse functional groups and is fast, catalytic and mild. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.144

文献信息

• Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3
  作者：Sudhir Kashyap、Srinivasa Rao Vidadala、Srinivas Hotha

  DOI：10.1016/j.tetlet.2007.10.144

  日期：2007.12

  C-2 Methylene glycosides were synthesized from C-2 propargyloxymethyl glycals in a stereoselective manner using a catalytic quantity of AuCl3. The Au-catalyzed reaction was explored using various aglycones. The current protocol enables the preparation of C-2 methylene glycosides, tolerates diverse functional groups and is fast, catalytic and mild. (c) 2007 Elsevier Ltd. All rights reserved.