(2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)-oxy)pentanoate | 1353654-51-9

• 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: (2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)-oxy)pentanoate
• 英文别名: benzyl (2S,3S)-2-amino-5-[(2-methylpropan-2-yl)oxycarbonylamino]-3-tri(propan-2-yl)silyloxypentanoate
• CAS: 1353654-51-9
• 化学式: C₂₆H₄₆N₂O₅Si
• 分子量: 494.747
• InChiKey: JTUQPFKTOQCWRN-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)-oxy)pentanoate 、 (三苯基膦烯)乙烯酮 以 甲苯 为溶剂， 反应 18.0h， 以27%的产率得到tert-butyl ((S)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-((triisopropylsilyl)oxy)propyl)carbamate
  参考文献：
  名称：

  Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.10.099
• 作为产物：
  描述：

  三异丙基氯硅烷 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 126.0h， 生成 (2S,3S)-benzyl 2-amino-5-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)-oxy)pentanoate
  参考文献：
  名称：

  Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.10.099

文献信息

• 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.