2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[10-(4-methoxy-benzyloxy)-decyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione | 1053627-72-7

• 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-[(2S,3S,4S,5R)-4-Benzyloxy-2-[10-(4-methoxy-benzyloxy)-decyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• 英文别名: 2-[(2S,3S,4S,5R)-2-[10-[(4-methoxyphenyl)methoxy]decyl]-5-[(2-methyl-1,3-dioxolan-2-yl)methyl]-4-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 1053627-72-7
• 化学式: C₄₃H₅₅NO₈
• 分子量: 713.912
• InChiKey: RAVUVVOGJJQWJK-KBJLFHOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[10-(4-methoxy-benzyloxy)-decyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 10.0h， 生成 2-[(2S,3S,4S,5R)-4-Benzyloxy-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 、 Wilkinson's catalyst 、 正丁基锂 、 二甲基硫 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 氢气 、 乙酸酐 、 戴斯-马丁氧化剂 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 原甲酸三乙酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 、 xylene 、 苯 为溶剂， -78.0~90.0 ℃ 、101.33 kPa 条件下， 反应 227.5h， 生成 2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[10-(4-methoxy-benzyloxy)-decyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-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

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.