benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxybutanoate | 1353655-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxybutanoate
• CAS: 1353655-04-5
• 化学式: C₃₅H₄₅NO₅Si
• 分子量: 587.832
• InChiKey: NDZWKTKGANWRBM-NYFMKLKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxybutanoate 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以81%的产率得到(2S,3R)-benzyl 2-amino-3-((triisopropylsilyl)oxy)butanoate
  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：

  Fmoc-Thr-OH 在 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 benzyl (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tri(propan-2-yl)silyloxybutanoate
  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