(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid cyanomethyl ester | 245674-56-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid cyanomethyl ester
• CAS: 245674-56-0
• 化学式: C₁₃H₂₅NO₃Si
• 分子量: 271.432
• InChiKey: YZCPSAJEUAMLQF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid cyanomethyl ester 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-2-Hydroxy-3-methyl-butyric acid (2R,3R,4R,5R)-5-{[(2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-phosphonooxymethyl-tetrahydro-furan-3-yloxy]-hydroxy-phosphoryloxymethyl}-2-(6-amino-purin-9-yl)-4-hydroxy-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Incorporation of esters into proteins: Improved synthesis of hydroxyacyl tRNAs

  摘要：

  We describe two synthetic advances in the preparation of acylated suppressor transfer RNAs which significantly enhance the ease with which alpha-hydroxy acids can be incorporated into protein structures using nonsense suppression methods. We demonstrate that, in most cases, protection of the alpha-hydroxy group in the acylation reaction is not necessary. In cases where protection of the alpha-hydroxy group is desired, we further demonstrate the efficacy of the TBDMS protecting group over the more standard o-nitrobenzyl-based protecting groups. These advances greatly simplify the protocol for incorporation of alpha-hydroxy acids into proteins, overcome limitations associated with photoreactive sidechains, and suggest a general approach to improved suppression yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01300-3
• 作为产物：
  描述：

  (S)-2-<(tert-butyldimethylsilyl)oxy>-3-methylbutanoic acid 、 氯乙腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid cyanomethyl ester
  参考文献：
  名称：

  Incorporation of esters into proteins: Improved synthesis of hydroxyacyl tRNAs

  摘要：

  We describe two synthetic advances in the preparation of acylated suppressor transfer RNAs which significantly enhance the ease with which alpha-hydroxy acids can be incorporated into protein structures using nonsense suppression methods. We demonstrate that, in most cases, protection of the alpha-hydroxy group in the acylation reaction is not necessary. In cases where protection of the alpha-hydroxy group is desired, we further demonstrate the efficacy of the TBDMS protecting group over the more standard o-nitrobenzyl-based protecting groups. These advances greatly simplify the protocol for incorporation of alpha-hydroxy acids into proteins, overcome limitations associated with photoreactive sidechains, and suggest a general approach to improved suppression yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01300-3