3,4,5-Trimethoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(S)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester | 1053747-42-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 3,4,5-Trimethoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(S)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester
• 英文别名: [(1R,2S,3R,4S)-4-hydroxy-1-[(2S)-oxiran-2-yl]-1,2-bis(phenylmethoxy)-5-[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]pentan-3-yl] 3,4,5-trimethoxybenzoate
• CAS: 1053747-42-4
• 化学式: C₆₅H₇₀O₁₄
• 分子量: 1075.26
• InChiKey: PVZBIDUSYFQPMU-HGQKAWIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  79
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,4,5-Trimethoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(S)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 3,4,5-Trimethoxy-benzoic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-hydroxymethyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 12. Synthesis and conformational analysis of .alpha.,.alpha.-, .alpha.,.beta.-, and .beta.,.beta.-C-trehaloses

  摘要：

  A single, unified strategy for the stereocontrolled synthesis of alpha,alpha-, alpha,beta-, and beta,beta-C-trehaloses (1-3) was developed. The solution conformations of C-trehaloses 1-3, as well as their permethyl derivatives, were determined on the basis of vicinal coupling constants observed in the H-1 NMR spectra. The preferred conformations for alpha,alpha- and beta,beta-C-trehaloses (1 and 3), shown in Figure 1, were predicted and experimentally proven. A diamond-lattice analysis of alpha,beta-C-trehalose (2), shown in Figure 2, revealed the relative stability of the three staggered conformers to be 2A > 2B > 2C, and the experimental data were found to be consistent with this trend. It was demonstrated that the inversion of the C.2 or C.2' hydroxyl group of 2 affected its conformational preference in a predictable manner; The H-1 NMR spectra of alpha,beta-C-trehalose 2 provided direct experimental evidence to illustrate that the alpha-C-glycosidic bond is conformationally more rigid than the beta-C-glycosidic bond,

  DOI：

  10.1021/jo00080a016
• 作为产物：
  描述：

  3,4,5-Trimethoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(S)-1-(4-methoxy-benzyloxy)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,4,5-Trimethoxy-benzoic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(S)-1-hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 12. Synthesis and conformational analysis of .alpha.,.alpha.-, .alpha.,.beta.-, and .beta.,.beta.-C-trehaloses

  摘要：

  A single, unified strategy for the stereocontrolled synthesis of alpha,alpha-, alpha,beta-, and beta,beta-C-trehaloses (1-3) was developed. The solution conformations of C-trehaloses 1-3, as well as their permethyl derivatives, were determined on the basis of vicinal coupling constants observed in the H-1 NMR spectra. The preferred conformations for alpha,alpha- and beta,beta-C-trehaloses (1 and 3), shown in Figure 1, were predicted and experimentally proven. A diamond-lattice analysis of alpha,beta-C-trehalose (2), shown in Figure 2, revealed the relative stability of the three staggered conformers to be 2A > 2B > 2C, and the experimental data were found to be consistent with this trend. It was demonstrated that the inversion of the C.2 or C.2' hydroxyl group of 2 affected its conformational preference in a predictable manner; The H-1 NMR spectra of alpha,beta-C-trehalose 2 provided direct experimental evidence to illustrate that the alpha-C-glycosidic bond is conformationally more rigid than the beta-C-glycosidic bond,

  DOI：

  10.1021/jo00080a016