diethyl phenylsulfonyl((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)methylphosphonate | 1193390-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl phenylsulfonyl((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)methylphosphonate
• 英文别名: (2R,3R,4S,5R,6R)-2-[benzenesulfonyl-[diethoxy(oxido)phosphaniumyl]methyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1193390-73-6
• 化学式: C₄₅H₅₁O₁₀PS
• 分子量: 814.934
• InChiKey: JUKIMRJTHXRMKJ-XCDRTOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  diethyl phenylsulfonyl((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)methylphosphonate 在 甲醇 、 sodium dihydrogenphosphate 、 sodium amalgam 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到diethyl ((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)methylphosphonate
  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 、 苯砜基甲基膦酸二乙酯 在 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 苯 为溶剂， 以39%的产率得到diethyl phenylsulfonyl((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)methylphosphonate
  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