(S)-benzyl 2-amino-3-((triisopropylsilyl)oxy)propanoate | 145790-72-3

• 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: (S)-benzyl 2-amino-3-((triisopropylsilyl)oxy)propanoate
• 英文别名: benzyl (2S)-2-amino-3-tri(propan-2-yl)silyloxypropanoate
• CAS: 145790-72-3
• 化学式: C₁₉H₃₃NO₃Si
• 分子量: 351.561
• InChiKey: RMVJGDLQVDWTEI-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  (S)-benzyl 2-amino-3-((triisopropylsilyl)oxy)propanoate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 (S)-2-[3-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-indol-5-yloxycarbonylamino]-3-triisopropylsilanyloxy-propionic acid
  参考文献：
  名称：

  Novel serine-based linker for the solid-phase synthesis of organic compounds

  摘要：

  A novel serine-derived Linker has been developed that allows phenolic templates to be cleaved from the resin with fluoride ion. The linker is stable to acids such as TFA and bases such as pyrrolidine. The linker should provide utility in multi-step solid phase organic chemistry protocols where both acid and base chemistry is used. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10618-9
• 作为产物：
  描述：

  三异丙基氯硅烷 、 丝氨酸苄酯盐酸盐 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到(S)-benzyl 2-amino-3-((triisopropylsilyl)oxy)propanoate
  参考文献：
  名称：

  Novel serine-based linker for the solid-phase synthesis of organic compounds

  摘要：

  A novel serine-derived Linker has been developed that allows phenolic templates to be cleaved from the resin with fluoride ion. The linker is stable to acids such as TFA and bases such as pyrrolidine. The linker should provide utility in multi-step solid phase organic chemistry protocols where both acid and base chemistry is used. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10618-9

文献信息

• Davies, John S.; Higginbotham, Clement L.; Tremeer, E. John, Journal of the Chemical Society. Perkin transactions I, 1992, # 22, p. 3043 - 3048
  作者：Davies, John S.、Higginbotham, Clement L.、Tremeer, E. John、Brown, Charles、Treadgold, Richard C.

  DOI：——

  日期：——
• Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
  作者：Inga Loke、Natja Park、Karl Kempf、Carsten Jagusch、Rainer Schobert、Sabine Laschat

  DOI：10.1016/j.tet.2011.10.099

  日期：2012.1

  alpha-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of beta-oxo functionalized alpha-aminoesters, e.g., esters of serine, threonine or beta-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the beta-OR group and on the configuration of beta-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel serine-based linker for the solid-phase synthesis of organic compounds
  作者：Yuo-Ling Chou、Michael M. Morrissey、Raju Mohan

  DOI：10.1016/s0040-4039(97)10618-9

  日期：1998.2

  A novel serine-derived Linker has been developed that allows phenolic templates to be cleaved from the resin with fluoride ion. The linker is stable to acids such as TFA and bases such as pyrrolidine. The linker should provide utility in multi-step solid phase organic chemistry protocols where both acid and base chemistry is used. (C) 1998 Elsevier Science Ltd. All rights reserved.