(4aR,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(2S)-3-oxo-3-phenylmethoxy-2-[[2-(4-phenylphenyl)acetyl]amino]propyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylic acid | 766514-67-4

• 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: (4aR,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(2S)-3-oxo-3-phenylmethoxy-2-[[2-(4-phenylphenyl)acetyl]amino]propyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylic acid
• CAS: 766514-67-4
• 化学式: C₃₃H₃₃NO₁₀S
• 分子量: 635.692
• InChiKey: AZDRMNPXMDFKPV-JJUXDXCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  197
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(2S)-3-oxo-3-phenylmethoxy-2-[[2-(4-phenylphenyl)acetyl]amino]propyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylic acid 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到(4aR,6R,7S,8S,8aR)-3-[(2S)-2-carboxy-2-[[2-(4-phenylphenyl)acetyl]amino]ethyl]-7,8-dihydroxy-6-(hydroxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylic acid
  参考文献：
  名称：

  A New Scaffold for the Stereoselective Synthesis of α-O-Linked Glycopeptide Mimetics

  摘要：

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.

  DOI：

  10.1021/jo049441h
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxy-butyric acid benzyl ester 在 吡啶 、 三甲基氯硅烷 、 phthalimidesulfenyl chloride 、 三乙胺 、 cesium fluoride 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 72.5h， 生成 (4aR,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(2S)-3-oxo-3-phenylmethoxy-2-[[2-(4-phenylphenyl)acetyl]amino]propyl]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine-2-carboxylic acid
  参考文献：
  名称：

  A New Scaffold for the Stereoselective Synthesis of α-O-Linked Glycopeptide Mimetics

  摘要：

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.

  DOI：

  10.1021/jo049441h

文献信息

• A New Scaffold for the Stereoselective Synthesis of α-<i>O</i>-Linked Glycopeptide Mimetics
  作者：Francesca Venturi、Chiara Venturi、Francesca Liguori、Martina Cacciarini、Monica Montalbano、Cristina Nativi

  DOI：10.1021/jo049441h

  日期：2004.9.1

  alpha-O-Linked glycohomoglutamates are obtained as diastereomerically pure compounds by chemo-, regio-, and stereoselective cycloadditions between glycals and aspartic acid derivatives. The latter constitute orthogonally functionalized scaffolds for glycopeptide mimetics.