(2S,3R,4R)-3,4-O-isopropylidene-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol | 1201913-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R)-3,4-O-isopropylidene-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol
• 英文别名: (1S)-1-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-difluoro-2-phenylselanylethanol
• CAS: 1201913-20-3
• 化学式: C₁₅H₁₈F₂O₃Se
• 分子量: 363.263
• InChiKey: GYKOSBNRGNMPEV-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以215 mg的产率得到(2S,3R,4R)-3,4-O-isopropylidene-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol
  参考文献：
  名称：

  Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides

  摘要：

  The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to alpha-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.079

文献信息

• Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses
  作者：Gaëlle Fourrière、Jérôme Lalot、Nathalie Van Hijfte、Jean-Charles Quirion、Eric Leclerc

  DOI：10.1016/j.tetlet.2009.09.170

  日期：2009.12

  The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes followed by a radical cyclization, and provides a secure strategy for a future synthesis of pentofuranoses and nucleoside analogues.

  描述了5-脱氧戊呋喃糖酶的二氟化碳环类似物的合成。该序列涉及将PhSeCF 2 TMS添加到碳水化合物衍生的醛中，然后进行自由基环化，并为将来合成戊呋喃糖酶和核苷类似物提供了安全的策略。