(1'S,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one | 250586-06-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1'S,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one
• 英文别名: (2S,5R)-5-[(S)-amino(phenyl)methyl]-2-tert-butyl-5-methyl-1,3-dioxolan-4-one
• CAS: 250586-06-2
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: IEZRFMVLEFIYGI-NJZAAPMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'S,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam
  参考文献：
  名称：

  New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-β-lactam

  摘要：

  A method is described for the chiral synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-beta-lactam, a useful precursor for the semi-synthesis of 2'-methyl-taxoids. This protocol follows Seebach's synthetic principle of 'self-regeneration of stereocenters' (SRS) and has been applied to addition reactions of the (2S)-chiral enolates of dioxolan-4-ones, derived from the acetalization of (S)-alpha-lactic acid and tert-butylaldehyde or pinacolone, to N-trimethylsilylphenyl aldimine. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00288-8
• 作为产物：
  描述：

  (2S,5R)-2-(tert-butyl)-5-(1'-benzylideneamino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one 在 盐酸 、 potassium carbonate 作用下， 生成 (1'R,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one 、 (1'S,2S,5R)-2-(tert-butyl)-5-(1'-amino-1'-phenylmethyl)-5-methyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-β-lactam

  摘要：

  A method is described for the chiral synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-beta-lactam, a useful precursor for the semi-synthesis of 2'-methyl-taxoids. This protocol follows Seebach's synthetic principle of 'self-regeneration of stereocenters' (SRS) and has been applied to addition reactions of the (2S)-chiral enolates of dioxolan-4-ones, derived from the acetalization of (S)-alpha-lactic acid and tert-butylaldehyde or pinacolone, to N-trimethylsilylphenyl aldimine. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00288-8

文献信息

• New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-β-lactam
  作者：Gaetano Barbaro、Arturo Battaglia、Fabio Di Giuseppe、Patrizia Giorgianni、Andrea Guerrini、Carlo Bertucci、Silvano Geremia

  DOI：10.1016/s0957-4166(99)00288-8

  日期：1999.7

  A method is described for the chiral synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-beta-lactam, a useful precursor for the semi-synthesis of 2'-methyl-taxoids. This protocol follows Seebach's synthetic principle of 'self-regeneration of stereocenters' (SRS) and has been applied to addition reactions of the (2S)-chiral enolates of dioxolan-4-ones, derived from the acetalization of (S)-alpha-lactic acid and tert-butylaldehyde or pinacolone, to N-trimethylsilylphenyl aldimine. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.