α-Mannopyranosyl β-C-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-Mannopyranosyl β-C-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]oxane-3,4,5-triol
• 化学式: C₁₃H₂₄O₁₀
• 分子量: 340.328
• InChiKey: SBKRKLSECOIJTA-AAWNBZOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  180
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-[(R)-1-hydroxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-3-(S)-oxiranyl-propyl ester 在 palladium dihydroxide 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 7.83h， 生成 α-Mannopyranosyl β-C-glucopyranoside
  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,