[2S,3R,4R]-4-(4-bromophenyl)-1-hydroxy-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate | 1215087-91-4

• 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,4R]-4-(4-bromophenyl)-1-hydroxy-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate
• 英文别名: [(2S,3R,4R)-4-(4-bromophenyl)-1-hydroxy-3-methyl-4-[(4-methylphenyl)sulfonylamino]butan-2-yl] acetate
• CAS: 1215087-91-4
• 化学式: C₂₀H₂₄BrNO₅S
• 分子量: 470.384
• InChiKey: SZKXZQTUDWKJPO-VHKYSDTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [2S,3R,4R,(S)R]-4-(4-bromophenyl)-1-(tert-butylsulfinyl)-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate 在 2,4,6-三甲基吡啶 、 三氟乙酸 、 potassium carbonate 、 sodium tetrahydroborate 作用下， 以 乙腈 、 水 为溶剂， 反应 0.33h， 以60%的产率得到[2S,3R,4R]-4-(4-bromophenyl)-1-hydroxy-3-methyl-4-(4-methylphenylsulfonamido)butan-2-yl acetate
  参考文献：
  名称：

  SmI2-coupling reaction of chiral non-racemic α-bromo-α′-sulfinyl ketones with imines: synthesis of enantiomerically pure 2-methyl-3-amino-1-ol moieties

  摘要：

  Chiral non-racemic alpha-bromo-alpha'-sulfinyl ketones were shown to react with imines in the presence of SmI2 to give the corresponding 1,3-aminoketo derivatives with good syn-diastereoselectivity. Further reduction of these adducts either with DIBAL-H only or with DIBAL-H in the presence of Yb(OTf)(3) afforded syn- and anti-2-methyl-3-amino-1-ol moieties, respectively, in good yields and diastereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.020