2-[(1S,2S,3S,4R,5R)-3-Benzyloxy-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl]-isoindole-1,3-dione | 163040-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[(1S,2S,3S,4R,5R)-3-Benzyloxy-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl]-isoindole-1,3-dione
• 英文别名: 2-[(1S,2S,3S,4R,5R)-2-(2-methylprop-2-enyl)-3-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]isoindole-1,3-dione
• CAS: 163040-76-4
• 化学式: C₂₅H₂₅NO₅
• 分子量: 419.477
• InChiKey: CTJCITGYLORFMM-QTXJXSEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-[(1S,2S,3S,4R,5R)-3-Benzyloxy-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl]-isoindole-1,3-dione 在 Wilkinson's catalyst 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 氢气 、 sodium hexamethyldisilazane 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 43.91h， 生成 2-[(2S,3S,4S,5S,6S)-4-Benzyloxy-6-benzyloxymethyl-2-[10-(4-methoxy-benzyloxy)-decyl]-5-(2-oxo-propyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Preferred Conformations of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II

  摘要：

  The syntheses of C-trisaccharides 1-4, carbon analogs of the human blood group determinant II-type II, have been achieved in a flexible and efficient manner. Vicinal coupling constants in the H-1 NMR spectrum provide experimental evidence that each of the four compounds 1-4 possesses a unique solution conformation, in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the influence of 1,3-diaxial like interactions about the C-aglyconic bond.

  DOI：

  10.1021/jo00112a040
• 作为产物：
  描述：

  (1S,2S,3S,4R,5R)-4-Azido-3-benzyloxy-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]octane 在 Lindlar's catalyst 吡啶 、 氢气 、 乙酸酐 作用下， 以 乙醇 为溶剂， 25.0~90.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 2-[(1S,2S,3S,4R,5R)-3-Benzyloxy-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Preferred Conformations of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II

  摘要：

  The syntheses of C-trisaccharides 1-4, carbon analogs of the human blood group determinant II-type II, have been achieved in a flexible and efficient manner. Vicinal coupling constants in the H-1 NMR spectrum provide experimental evidence that each of the four compounds 1-4 possesses a unique solution conformation, in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the influence of 1,3-diaxial like interactions about the C-aglyconic bond.

  DOI：

  10.1021/jo00112a040

文献信息

• Preferred Conformations of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II
  作者：Alexander Wei、Arnaud Haudrechy、Catharine Audin、Hyuk-Sang Jun、Nathalie Haudrechy-Bretel、Yoshito Kishi

  DOI：10.1021/jo00112a040

  日期：1995.4

  The syntheses of C-trisaccharides 1-4, carbon analogs of the human blood group determinant II-type II, have been achieved in a flexible and efficient manner. Vicinal coupling constants in the H-1 NMR spectrum provide experimental evidence that each of the four compounds 1-4 possesses a unique solution conformation, in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the influence of 1,3-diaxial like interactions about the C-aglyconic bond.