tert-butyl ((S)-3-(benzyloxy)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)propyl)carbamate | 1353654-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl ((S)-3-(benzyloxy)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)propyl)carbamate
• 英文别名: tert-butyl N-[(3S)-3-[(2S)-5-oxo-3-phenylmethoxy-1,2-dihydropyrrol-2-yl]-3-phenylmethoxypropyl]carbamate
• CAS: 1353654-91-7
• 化学式: C₂₆H₃₂N₂O₅
• 分子量: 452.55
• InChiKey: VAFJWBANGFFKKH-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,3S)-benzyl 2-azido-5-(tert-butoxycarbonylamino)-3-hydroxypentanoate 在 甲醇 、 tin(ll) chloride 、 silver(l) oxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 41.0h， 生成 tert-butyl ((S)-3-(benzyloxy)-3-((S)-3-(benzyloxy)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)propyl)carbamate 、 (2S,3S)-benzyl 2-acetamido-3-(benzyloxy)-5-((tert-butoxycarbonyl)amino)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.