(2R,3S)-3-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]-N,N-dimethyloxirane-2-carboxamide | 220859-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]-N,N-dimethyloxirane-2-carboxamide
• CAS: 220859-00-7
• 化学式: C₁₉H₃₇NO₅Si
• 分子量: 387.592
• InChiKey: AYHKLVXTVGRMNF-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]-N,N-dimethyloxirane-2-carboxamide 生成 (2S,3S,4S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethyl-pentanoic acid dimethylamide
  参考文献：
  名称：

  Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes

  摘要：

  Reactions of stabilized sulfur ylides with chiral aldehydes provided epoxides with high stereoselectivity. The opening of the resulting epoxides with lithium dimethyl cuprate gave 2-methyl-3-hydroxy amides which represent potentially useful building blocks for the synthesis of macrolide natural products. These amides were transformed into chiral aldehydes, with a methyl group in the alpha-position, and were reacted, in a iterative process, with a sulfur ylide reagent to give, in high yield and stereoselectivity, the epoxides with the stereochemistry according to Felkin-Ahn control. Finally, opening of the epoxide with the Oilman reagent provided a compound with four stereocenters occurring in the macrolide-type of natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02613-6
• 作为产物：
  描述：

  (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol 生成 (2R,3S)-3-[(1S,2S)-1-[tert-butyl(dimethyl)silyl]oxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-2-yl]-N,N-dimethyloxirane-2-carboxamide
  参考文献：
  名称：

  Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes

  摘要：

  Reactions of stabilized sulfur ylides with chiral aldehydes provided epoxides with high stereoselectivity. The opening of the resulting epoxides with lithium dimethyl cuprate gave 2-methyl-3-hydroxy amides which represent potentially useful building blocks for the synthesis of macrolide natural products. These amides were transformed into chiral aldehydes, with a methyl group in the alpha-position, and were reacted, in a iterative process, with a sulfur ylide reagent to give, in high yield and stereoselectivity, the epoxides with the stereochemistry according to Felkin-Ahn control. Finally, opening of the epoxide with the Oilman reagent provided a compound with four stereocenters occurring in the macrolide-type of natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02613-6

文献信息

• Epoxyamide-Based Strategy for the Synthesis of Polypropionate-Type Frameworks
  作者：Francisco Sarabia、Francisca Martín-Gálvez、Miguel García-Castro、Samy Chammaa、Antonio Sánchez-Ruiz、José F. Tejón-Blanco

  DOI：10.1021/jo801728s

  日期：2008.11.21

  A new approach to the stereoselective synthesis of polypropionate-type frameworks is reported utilizing reactions of amide-stabilized sulfur ylides with chiral aldehydes. To establish a new strategy for macrolide fragment synthesis, the stereoselectivity of these reactions in the construction of epoxy amides was the most important aspect of this study. In this aspect, we found a strong influence of

  据报道，利用酰胺稳定的硫酰化物与手性醛的反应，可以合成一种新的聚丙烯酸酯类骨架立体选择合成方法。为了建立大环内酯片段合成的新策略，这些反应在环氧酰胺的构建中的立体选择性是这项研究的最重要方面。在这方面，我们发现起始醛中使用的保护基对其与硫代叶立德1反应的立体化学结果具有强烈影响。因此，与其他醛相比，许多醛显示出显着的立体分化，从而提供了主要的非对映异构体立体选择性差或没有。尽管在某些情况下在非对映异构体产量方面遇到了困难，