(R(S),2S,3R,4R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-1-phenylselanyl-hex-5-ene | 1233949-12-6

• 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: (R(S),2S,3R,4R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-1-phenylselanyl-hex-5-ene
• CAS: 1233949-12-6
• 化学式: C₃₀H₃₅F₂NO₃SSe
• 分子量: 606.636
• InChiKey: YYKNNVZIDWSBDS-OWVFQEMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  [difluoro(phenylseleno)methyl]trimethylsilane 、 (R(S))-N-[(2R,3R)-2,3-bis(benzyloxy)pent-4-enylidene]-tert-butanesulfinamide 在 TBAT 、 水 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (R(S),2R,3R,4R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-1-phenylselanyl-hex-5-ene 、 (R(S),2S,3R,4R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-1-phenylselanyl-hex-5-ene
  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