(S)-tert-butyl (1,4-dihydroxy-4-methylpentan-2-yl)carbamate | 1416253-35-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-tert-butyl (1,4-dihydroxy-4-methylpentan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2S)-1,4-dihydroxy-4-methylpentan-2-yl]carbamate
• CAS: 1416253-35-4
• 化学式: C₁₁H₂₃NO₄
• 分子量: 233.308
• InChiKey: QEQOFIHOZTWWQG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (1,4-dihydroxy-4-methylpentan-2-yl)carbamate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 间氯过氧苯甲酸 、 sodium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 5.0~60.0 ℃ 、413.7 kPa 条件下， 反应 23.5h， 生成 (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)succinic acid
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g
• 作为产物：
  描述：

  (S)-3-(BOC-氨基)-4-羟基丁酸甲酯 、 碘甲烷 在 magnesium 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到(S)-tert-butyl (1,4-dihydroxy-4-methylpentan-2-yl)carbamate
  参考文献：
  名称：

  Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

  摘要：

  For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.

  DOI：

  10.1021/jo302203g

文献信息

• US8906853B2
  申请人：——

  公开号：US8906853B2

  公开（公告）日：2014-12-09
• [EN] NOVEL [N-ME-4-HYDROXYLEUCINE]-9-CYCLOSPORIN ANALOGUES<br/>[FR] NOUVEAUX ANALOGUES DE [N-ME-4-HYDROXYLEUCINE]-9-CYCLOSPORINE
  申请人：ENANTA PHARM INC

  公开号：WO2014085623A1

  公开（公告）日：2014-06-05

  The present invention relates to novel cyclosporine analogues having antiviral activity against HCV and useful in the treatment of HCV infections. More particularly, the invention relates to novel cyclosporine analogue compounds, compositions containing such compounds and methods for using the same, as well as processes for making such compounds.