(2S,3R,4S)-3,4-bis(O-methoxymethyl)-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol | 1233948-94-1

• 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: (2S,3R,4S)-3,4-bis(O-methoxymethyl)-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol
• CAS: 1233948-94-1
• 化学式: C₁₆H₂₂F₂O₅Se
• 分子量: 411.304
• InChiKey: FGRALSPZDPNBSS-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  [difluoro(phenylseleno)methyl]trimethylsilane 、 (2R,3S)-2,3-bis(methoxymethoxy)pent-4-enal 在 四甲基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2R,3R,4S)-3,4-bis(O-methoxymethyl)-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol 、 (2S,3R,4S)-3,4-bis(O-methoxymethyl)-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