((1S,2S)-3-Bromo-2-hydroxy-1-isopropyl-propyl)-carbamic acid benzyl ester | 362610-35-3

• 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: ((1S,2S)-3-Bromo-2-hydroxy-1-isopropyl-propyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S,3S)-1-bromo-2-hydroxy-4-methylpentan-3-yl]carbamate
• CAS: 362610-35-3
• 化学式: C₁₄H₂₀BrNO₃
• 分子量: 330.222
• InChiKey: RRPRCDOBDXGZAS-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1S,2S)-3-Bromo-2-hydroxy-1-isopropyl-propyl)-carbamic acid benzyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到((S)-2-Methyl-1-oxiranyl-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Highly Stereoselective Synthesis of anti-N-Protected-α-Amino Epoxides

  摘要：

  A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a beta -ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.

  DOI：

  10.1021/jo010319h
• 作为产物：
  描述：

  (3-bromo-1-(S)-(1-methylethyl)-2-oxopropyl)carbamic acid benzyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.33h， 生成 ((1S,2S)-3-Bromo-2-hydroxy-1-isopropyl-propyl)-carbamic acid benzyl ester 、 ((1S,2R)-3-Bromo-2-hydroxy-1-isopropyl-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Highly Stereoselective Synthesis of anti-N-Protected-α-Amino Epoxides

  摘要：

  A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a beta -ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.

  DOI：

  10.1021/jo010319h

文献信息

• Highly Stereoselective Synthesis of <i>an</i><i>ti</i>-N-Protected-α-Amino Epoxides
  作者：Robert V. Hoffman、Warren S. Weiner、Najib Maslouh

  DOI：10.1021/jo010319h

  日期：2001.8.1

  A simple and efficient method for the synthesis of anti-N-protected amino epoxides from carbamate-protected amino acids is described. The two key steps are the monobromination of a beta -ketoester and chelation-controlled reduction of a bromomethyl ketone intermediate. Good overall yields, high diastereoselectivity, and excellent functional group compatibility are characteristic.