(2S,3S,4S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-butane-1,2,3-triol | 145852-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-butane-1,2,3-triol
• 英文别名: (2S,3S,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxy-2-[[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]butane-1,2,3-triol
• CAS: 145852-88-6
• 化学式: C₅₁H₆₀O₁₁
• 分子量: 849.031
• InChiKey: VEAMHUJCMVYXGG-NHIBLZKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-butane-1,2,3-triol 在 吡啶 、 咪唑 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,3S,4S,5R)-4-Benzyloxy-2,5-bis-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 11. C-Sucrose: new practical synthesis, structural reassignment, and solid-state and solution conformation of its octaacetate

  摘要：

  The stereochemistry of C-sucrose, previously reported from this laboratory, was revised as epi-C.2'-C-sucrose (5) from H-1 NOE measurements on octaacetates 2 and 6 and an X-ray analysis of 2. A new, stereospecific, and practical synthesis of C-sucrose (1) was developed. The solid-state conformation and solution behavior of the octaacetate 2 of C-sucrose were compared with the corresponding octaacetate 4 of parent sucrose.

  DOI：

  10.1021/jo00054a006
• 作为产物：
  描述：

  (1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol 在 吡啶 、 四氧化锇 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-butane-1,2,3-triol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 11. C-Sucrose: new practical synthesis, structural reassignment, and solid-state and solution conformation of its octaacetate

  摘要：

  The stereochemistry of C-sucrose, previously reported from this laboratory, was revised as epi-C.2'-C-sucrose (5) from H-1 NOE measurements on octaacetates 2 and 6 and an X-ray analysis of 2. A new, stereospecific, and practical synthesis of C-sucrose (1) was developed. The solid-state conformation and solution behavior of the octaacetate 2 of C-sucrose were compared with the corresponding octaacetate 4 of parent sucrose.

  DOI：

  10.1021/jo00054a006

文献信息

• Preferred conformation of C-glycosides. 11. C-Sucrose: new practical synthesis, structural reassignment, and solid-state and solution conformation of its octaacetate
  作者：Daniel J. O'Leary、Yoshito Kishi

  DOI：10.1021/jo00054a006

  日期：1993.1

  The stereochemistry of C-sucrose, previously reported from this laboratory, was revised as epi-C.2'-C-sucrose (5) from H-1 NOE measurements on octaacetates 2 and 6 and an X-ray analysis of 2. A new, stereospecific, and practical synthesis of C-sucrose (1) was developed. The solid-state conformation and solution behavior of the octaacetate 2 of C-sucrose were compared with the corresponding octaacetate 4 of parent sucrose.