Acetic acid (2S,3S,4R,5S,6R)-4-acetoxy-6-fluoro-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester | 113119-44-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4R,5S,6R)-4-acetoxy-6-fluoro-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4R,5S,6R)-4-acetyloxy-6-fluoro-5-iodo-2-methyloxan-3-yl] acetate
• CAS: 113119-44-1
• 化学式: C₁₀H₁₄FIO₅
• 分子量: 360.121
• InChiKey: ZOKRKOFMLWRQFI-BISAVSQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 p-iodotoluene difluoride 、 碘 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到Acetic acid (2S,3S,4R,6S)-4-acetoxy-6-fluoro-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Iodofluorination of alkenes and alkynes promoted by iodine and 4-iodotoluene difluoride

  摘要：

  It was found that a mixture of molecular iodine and 4-iodotoluene difluoride are useful to generate in situ the couple 'IF' that was able to add in a Markovnikov fashion and with prevalent anti-stereoselectivity to various alkenes and alkynes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.029

文献信息

• Iodofluorination of Alkenes Using Bis(<i>sym</i>-collidine)iodine(I) Tetrafluoroborate
  作者：Robert D. Evans、J. Herman Schauble

  DOI：10.1055/s-1987-27999

  日期：——

  I+(Collidine)2BF4 - in dichloromethane has been found to be a convenient reagent for regio- and stereospecific conversion of a variety of cycloalkenes to vicinal trans-iodofluorocycloalkanes. With bicyclo[2.2.1]heptene and bicyclo[2.2.1]heptadiene, only tricyclic products were obtained. Application of the title reagent to certain glycal esters provides a new method for stereoselective synthesis of trans-diaxial iodopyranosyl fluorides.

  I+(Collidine)2BF4 - 在二氯甲烷中被发现是一种便捷的试剂，可用于多种环烯烃的区域选择性和立体选择性转化为邻位反式碘氟环烯烃。对于双环[2.2.1]庚烯和双环[2.2.1]庚二烯，仅获得了三环产品。将该试剂应用于某些糖醇酯提供了一种新的立体选择性合成反式双轴碘吡喃糖基氟化物的方法。