(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde | 220858-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde
• 英文别名: (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropanal
• CAS: 220858-87-7
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: UYEUGWBIICUXHQ-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde 生成 (2S,3S,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-N,N,2,4-tetramethylpentanamide
  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,3R,4R)-N,N-Dimethyl-2,3-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentanoamide 在 三乙基硼氢化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde
  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

• A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
  作者：Francisco Sarabia、Samy Chammaa、Miguel García-Castro、Francisca Martín-Gálvez

  DOI：10.1039/b912070j

  日期：——

  A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of transepoxyamides under very mild reaction conditions.

  一种新型手性硫叶立德被合成，并测试了其对羰基化合物的反应活性，结果表明在非常温和的反应条件下，生成transepoxy酰胺具有高度的立体选择性。
• 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，
• Stereoselective synthesis of precursors of the macrolide antibiotics via reactions of sulfur ylides with chiral aldehydes
  作者：F.Jorge López-Herrera、Francisco Sarabia-García、Gracia María Pedraza-Cebrián、María Soledad Pino-González

  DOI：10.1016/s0040-4039(98)02613-6

  日期：1999.2

  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.