(2S,3S)-2-Benzyloxycarbonylamino-3-methyl-4-oxo-4-phenyl-butyric acid tert-butyl ester | 190579-76-1

• 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: (2S,3S)-2-Benzyloxycarbonylamino-3-methyl-4-oxo-4-phenyl-butyric acid tert-butyl ester
• 英文别名: tert-butyl (2S,3S)-3-methyl-4-oxo-4-phenyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 190579-76-1
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: HHDGASMDUGTSBH-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-Benzyloxycarbonylamino-3-methyl-4-oxo-4-phenyl-butyric acid tert-butyl ester 在 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ((3S,4R,5R)-4-Methyl-2-oxo-5-phenyl-tetrahydro-furan-3-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of all Stereoisomeric 2-Amino-3-Hydroxy-4-Phenylbutanolides

  摘要：

  Diastereoselective methylation of the ketone 5a leads to the anti-derivative 4a; the other diastereoisomer 4b may be obtained by a deprotonation/reprotonation sequence. Each of the methylated products may be reduced stereoselectively in either sense by appropriate choice of reagent, providing a route to all stereoisomers of the title 2-amino-3-hydroxy-4-phenylbutanolides 10a-d. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00544-3
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonylamino-4-oxo-4-phenyl-butyric acid tert-butyl ester 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到(2S,3R)-2-Benzyloxycarbonylamino-3-methyl-4-oxo-4-phenyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of all Stereoisomeric 2-Amino-3-Hydroxy-4-Phenylbutanolides

  摘要：

  Diastereoselective methylation of the ketone 5a leads to the anti-derivative 4a; the other diastereoisomer 4b may be obtained by a deprotonation/reprotonation sequence. Each of the methylated products may be reduced stereoselectively in either sense by appropriate choice of reagent, providing a route to all stereoisomers of the title 2-amino-3-hydroxy-4-phenylbutanolides 10a-d. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00544-3

文献信息

• Stereoselective Synthesis of all Stereoisomeric 2-Amino-3-Hydroxy-4-Phenylbutanolides
  作者：Susan Gair、Richard F.W Jackson*、Paul A Brown

  DOI：10.1016/s0040-4039(97)00544-3

  日期：1997.4

  Diastereoselective methylation of the ketone 5a leads to the anti-derivative 4a; the other diastereoisomer 4b may be obtained by a deprotonation/reprotonation sequence. Each of the methylated products may be reduced stereoselectively in either sense by appropriate choice of reagent, providing a route to all stereoisomers of the title 2-amino-3-hydroxy-4-phenylbutanolides 10a-d. (C) 1997 Elsevier Science Ltd.