(1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol | 115117-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol
• 英文别名: (1S,2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxy-1-[(2S)-2-[[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxiran-2-yl]ethanol
• CAS: 115117-20-9
• 化学式: C₅₁H₅₈O₁₀
• 分子量: 831.016
• InChiKey: XTISQUCIIHVFBL-NHIBLZKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  61
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol 在 camphor-10-sulfonic acid 、 水 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到(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：

  Synthesis of C-sucrose

  摘要：

  DOI：

  10.1021/jo00249a056
• 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 、 咪唑 、 四氧化锇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol
  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

• DYER, U. C.;KISHI, YOSHITO, J. ORG. CHEM., 53,(1988) N 14, 3383-3384
  作者：DYER, U. C.、KISHI, YOSHITO

  DOI：——

  日期：——
• Synthesis of C-sucrose
  作者：Ulrich C. Dyer、Yoshito Kishi

  DOI：10.1021/jo00249a056

  日期：1988.7
• 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.