(S(S),2S,3R,4R,5R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-5-methylcyclopentane | 1233949-23-9

• 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: (S(S),2S,3R,4R,5R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-5-methylcyclopentane
• CAS: 1233949-23-9
• 化学式: C₂₄H₃₁F₂NO₃S
• 分子量: 451.578
• InChiKey: JMFQHVJCLPVZNK-YCGVAERESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S(S),2R,3R,4R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-1-phenylselanyl-hex-5-ene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 叔丁醇 为溶剂， 生成 (S(S),2S,3R,4R,5R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-5-methylcyclopentane 、 (S(S),2S,3R,4R,5S)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-5-methylcyclopentane
  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