(2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(phenylaminoxy)butan-1-ol | 1360074-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(phenylaminoxy)butan-1-ol
• 英文别名: (2R,3S)-2-anilinooxy-3-[tert-butyl(dimethyl)silyl]oxybutan-1-ol
• CAS: 1360074-14-1
• 化学式: C₁₆H₂₉NO₃Si
• 分子量: 311.497
• InChiKey: QLXJNPZEBXYVAT-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(phenylaminoxy)butan-1-ol 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 (2R,3S)-3-[(tert-butyldimethyl)silyloxy]-1,2-epoxybutane
  参考文献：
  名称：

  Synthesis of chiral 1,2,3-triols via organocatalyzed α-hydroxylation of protected β-hydroxyaldehydes

  摘要：

  Protected 1,2,3-triols were prepared by organocatalytic alpha-hydroxylation of beta-hydroxyaldehydes followed by in situ reduction. All diastereoisomers were obtained with correct yields and good to excellent de. The absolute configurations of the new asymmetric centers were confirmed by derivatization into the corresponding epoxide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.078
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(phenylaminoxy)butan-1-ol
  参考文献：
  名称：

  Synthesis of chiral 1,2,3-triols via organocatalyzed α-hydroxylation of protected β-hydroxyaldehydes

  摘要：

  Protected 1,2,3-triols were prepared by organocatalytic alpha-hydroxylation of beta-hydroxyaldehydes followed by in situ reduction. All diastereoisomers were obtained with correct yields and good to excellent de. The absolute configurations of the new asymmetric centers were confirmed by derivatization into the corresponding epoxide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.078