2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile | 1193390-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile
• 英文别名: 2-(benzenesulfonyl)-2-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetonitrile
• CAS: 1193390-72-5
• 化学式: C₄₂H₄₁NO₇S
• 分子量: 703.856
• InChiKey: UKXIFADNQCCTOV-HPDHVYSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile 在 甲醇 、 magnesium 作用下， 反应 18.0h， 以70%的产率得到2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile
  参考文献：
  名称：

  A Mitsunobu route to C-glycosides

  摘要：

  C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach toward the synthesis of C-glycolipids is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.024
• 作为产物：
  描述：

  2,3,4,6-四-o-苄基-D-吡喃葡萄糖 、 苯磺酰乙腈 在 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 苯 为溶剂， 以62%的产率得到2-(phenylsulfonyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetonitrile
  参考文献：
  名称：

  A Mitsunobu route to C-glycosides

  摘要：

  C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach toward the synthesis of C-glycolipids is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.024