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 | 163040-83-3

• 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-oxo-propyl)-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-oxopropyl)-4-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 163040-83-3
• 化学式: C₄₁H₅₁NO₇
• 分子量: 669.858
• InChiKey: DURSQHPNMSPKOF-QCIAYHCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde 、 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 在 正丁基锂 、 六甲基二硅氮烷 作用下， 生成 2-{(2S,3S,4S,5R)-4-Benzyloxy-5-[(4R,5R,6R)-5,7-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-oxo-heptyl]-2-[10-(4-methoxy-benzyloxy)-decyl]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 、 2-{(2S,3S,4S,5R)-4-Benzyloxy-5-[(4S,5R,6R)-5,7-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-oxo-heptyl]-2-[10-(4-methoxy-benzyloxy)-decyl]-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：

  Acetic acid (2S,3R,4S,5S,6S)-6-acetoxymethyl-4-benzyloxy-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-(2-methyl-allyl)-tetrahydro-pyran-2-yl ester 在 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 、 氢气 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 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 、 水 、 丙酮 、 乙腈 、 xylene 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 210.42h， 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

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.