(4S)-3-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(S)-4-benzyloxybutan-2-yl]oxazolidin-5-one | 699020-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (4S)-3-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(S)-4-benzyloxybutan-2-yl]oxazolidin-5-one
• 英文别名: 9H-fluoren-9-ylmethyl (4S)-5-oxo-4-[(2S)-4-phenylmethoxybutan-2-yl]-1,3-oxazolidine-3-carboxylate
• CAS: 699020-36-5
• 化学式: C₂₉H₂₉NO₅
• 分子量: 471.553
• InChiKey: QUTFCTXWNJCPGE-DCFHFQCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(S)-4-benzyloxybutan-2-yl]oxazolidin-5-one 在 三乙基硅烷 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以21%的产率得到(2S,3S)-5-benzyloxy-2-[(9H-fluoren-9-ylmethoxycarbonyl)methylamino]-3-methylpentanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-δ-hydroxyisoleucine, noncoded amino acid of halipeptin A

  摘要：

  The first enantio selective synthesis of N,O-diprotected(2S,3S)-N-methyl-delta-hydroxyisoleucine 4, starting from readily available (tert-butyldimethylsilyl)-2-butyn-1-ol 5, is described. The key steps of this stereochemical flexible synthetic route involve a silyl-assisted [3,3]-sigmatropic rearrangement, for the establishment of the correct stereoisomeric pattern, and a triethylsilane-TFA induced reduction of an oxazolidinone intermediate, to yield the requested N-methylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.008
• 作为产物：
  描述：

  Fmoc-4,5-didehydroisoleucine 在 dimethyl sulfide borane 、 碳酸氢钠 、 对甲苯磺酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 38.0h， 生成 (4S)-3-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(S)-4-benzyloxybutan-2-yl]oxazolidin-5-one
  参考文献：
  名称：

  Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-δ-hydroxyisoleucine, noncoded amino acid of halipeptin A

  摘要：

  The first enantio selective synthesis of N,O-diprotected(2S,3S)-N-methyl-delta-hydroxyisoleucine 4, starting from readily available (tert-butyldimethylsilyl)-2-butyn-1-ol 5, is described. The key steps of this stereochemical flexible synthetic route involve a silyl-assisted [3,3]-sigmatropic rearrangement, for the establishment of the correct stereoisomeric pattern, and a triethylsilane-TFA induced reduction of an oxazolidinone intermediate, to yield the requested N-methylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.008

文献信息

• Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methyl-δ-hydroxyisoleucine, noncoded amino acid of halipeptin A
  作者：Irene Izzo、Elvira Avallone、Luca Della Corte、Nakia Maulucci、Francesco De Riccardis

  DOI：10.1016/j.tetasy.2004.02.008

  日期：2004.4

  The first enantio selective synthesis of N,O-diprotected(2S,3S)-N-methyl-delta-hydroxyisoleucine 4, starting from readily available (tert-butyldimethylsilyl)-2-butyn-1-ol 5, is described. The key steps of this stereochemical flexible synthetic route involve a silyl-assisted [3,3]-sigmatropic rearrangement, for the establishment of the correct stereoisomeric pattern, and a triethylsilane-TFA induced reduction of an oxazolidinone intermediate, to yield the requested N-methylation. (C) 2004 Elsevier Ltd. All rights reserved.