9H-fluoren-9-ylmethyl (2R,3S,4S)-2-(hydroxymethyl)-3,4-bis(2-methoxyethoxymethoxy)pyrrolidine-1-carboxylate | 868159-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl (2R,3S,4S)-2-(hydroxymethyl)-3,4-bis(2-methoxyethoxymethoxy)pyrrolidine-1-carboxylate
• CAS: 868159-63-1
• 化学式: C₂₈H₃₇NO₉
• 分子量: 531.603
• InChiKey: PZEXSXZUSZCXBL-PVHODMMVSA-N

物化性质

• 沸点：
  643.1±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl (2R,3S,4S)-2-(hydroxymethyl)-3,4-bis(2-methoxyethoxymethoxy)pyrrolidine-1-carboxylate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 sodium chlorite 、 sodium dihydrogenphosphate 、 氢溴酸 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 18.0h， 生成 (2S,3S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-3,4-dihydroxypyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  The conversion of pentoses to 3,4-dihydroxyprolines

  摘要：

  The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproli ne was synthesized from L-arabinose in 10 steps and 31 % overall yield. The same series of reactions was employed to convert L-xylose to L-2,3trans-3,4-trans-3,4-dihydroxyproline. Orthogonally protected versions of these amino acids were produced on gram scale, en route to the free amino acids, and these will serve as versatile intermediates in peptide synthesis. This synthetic strategy involved N alpha-Fmoc protection and protection of the C3 and C4 secondary alcohols as methoxyethoxymethyl (MEM) ethers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.072
• 作为产物：
  描述：

  L-阿拉伯糖 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 、 甲酸 、 氢气 、 溴 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 反应 147.0h， 生成 9H-fluoren-9-ylmethyl (2R,3S,4S)-2-(hydroxymethyl)-3,4-bis(2-methoxyethoxymethoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  The conversion of pentoses to 3,4-dihydroxyprolines

  摘要：

  The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproli ne was synthesized from L-arabinose in 10 steps and 31 % overall yield. The same series of reactions was employed to convert L-xylose to L-2,3trans-3,4-trans-3,4-dihydroxyproline. Orthogonally protected versions of these amino acids were produced on gram scale, en route to the free amino acids, and these will serve as versatile intermediates in peptide synthesis. This synthetic strategy involved N alpha-Fmoc protection and protection of the C3 and C4 secondary alcohols as methoxyethoxymethyl (MEM) ethers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.072

文献信息

• The conversion of pentoses to 3,4-dihydroxyprolines
  作者：Carol M. Taylor、Chantelle E. Jones、Kristin Bopp

  DOI：10.1016/j.tet.2005.07.072

  日期：2005.10

  The synthesis of two naturally-occurring isomers of 3,4-dihydroxyproline is reported. L-2,3-cis-3,4-trans-3,4-Dihydroxyproli ne was synthesized from L-arabinose in 10 steps and 31 % overall yield. The same series of reactions was employed to convert L-xylose to L-2,3trans-3,4-trans-3,4-dihydroxyproline. Orthogonally protected versions of these amino acids were produced on gram scale, en route to the free amino acids, and these will serve as versatile intermediates in peptide synthesis. This synthetic strategy involved N alpha-Fmoc protection and protection of the C3 and C4 secondary alcohols as methoxyethoxymethyl (MEM) ethers. (c) 2005 Elsevier Ltd. All rights reserved.