(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4R,5R,6R)-6-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4,5-bis(phenylmethoxy)-2-[[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]oxan-3-ol
• 化学式: C₇₅H₇₆O₁₁
• 分子量: 1153.42
• InChiKey: VKZSYBCDNYVYDJ-SBMJCPQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  86
• 可旋转键数：
  28
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-ol 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (2R,3S,4R,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-ol
  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：

  2-O-benzyl-3,4-O-isopropylidene-L-threitol 在 Lindlar's catalyst 、 palladium-lead 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 3 A molecular sieve 、 硼烷 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 溶剂黄146 、 cesium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 nickel dichloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -35.0~50.0 ℃ 、101.33 kPa 条件下， 反应 151.58h， 生成 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-3-ol
  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

文献信息

• Preferred conformation of C-glycosides. 12. Synthesis and conformational analysis of .alpha.,.alpha.-, .alpha.,.beta.-, and .beta.,.beta.-C-trehaloses
  作者：Alexander Wei、Yoshito Kishi

  DOI：10.1021/jo00080a016

  日期：1994.1

  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,