(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(bis(phenylsulfonyl)methyl)tetrahydro-2H-pyran | 1193390-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(bis(phenylsulfonyl)methyl)tetrahydro-2H-pyran
• 英文别名: (2R,3R,4S,5R,6R)-2-[bis(benzenesulfonyl)methyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1193390-71-4
• 化学式: C₄₇H₄₆O₉S₂
• 分子量: 819.009
• InChiKey: PIYBMOKSZPQMBG-JFPKXAKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(bis(phenylsulfonyl)methyl)tetrahydro-2H-pyran 在 水 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以100%的产率得到(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(phenylsulfonylmethyl)tetrahydro-2H-pyran
  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 、 双苯磺酸甲烷 在 三丁基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以84%的产率得到(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(bis(phenylsulfonyl)methyl)tetrahydro-2H-pyran
  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

文献信息

• A Mitsunobu route to C-glycosides
  作者：Paolo Pasetto、Matthew C. Walczak

  DOI：10.1016/j.tet.2009.08.024

  日期：2009.10

  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.