3,4-isopropylidine-1,6-bis-p-tolylsulfonyl-D-mannitol | 1096364-58-7

• 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: 3,4-isopropylidine-1,6-bis-p-tolylsulfonyl-D-mannitol
• 英文别名: (1S)-1-[(4R,5R)-5-[(1S)-1-hydroxy-2-(4-methylphenyl)sulfonylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methylphenyl)sulfonylethanol
• CAS: 1096364-58-7
• 化学式: C₂₃H₃₀O₈S₂
• 分子量: 498.618
• InChiKey: OJIJQCYKPGIOCD-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-isopropylidine-1,6-bis-p-tolylsulfonyl-D-mannitol 在 吡啶 、 甲基磺酰氯 作用下， 以65%的产率得到(4R,5R)-2,2-dimethyl-4,5-bis[(E)-2-(p-tolylsulfonyl)ethenyl]-1,3-dioxolane
  参考文献：
  名称：

  Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates

  摘要：

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.

  DOI：

  10.1021/jo801948m
• 作为产物：
  描述：

  (1S)-1-[(4R,5R)-5-[(1S)-1-hydroxy-2-(4-methylphenyl)sulfanylethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methylphenyl)sulfanylethanol 在 magnesium bis(monoperoxyphthalate)hexahydrate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以80%的产率得到3,4-isopropylidine-1,6-bis-p-tolylsulfonyl-D-mannitol
  参考文献：
  名称：

  Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates

  摘要：

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.

  DOI：

  10.1021/jo801948m

文献信息

• Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates
  作者：Rahul Bhattacharya、Ananta Kumar Atta、Debanjana Dey、Tanmaya Pathak

  DOI：10.1021/jo801948m

  日期：2009.1.16

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.