bis(β-D-glucopyranosyl)methane | 144791-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(β-D-glucopyranosyl)methane
• 英文别名: β,β-C-Trehalose；C-β,β-trehalose；(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]oxane-3,4,5-triol
• CAS: 144791-36-6
• 化学式: C₁₃H₂₄O₁₀
• 分子量: 340.328
• InChiKey: SBKRKLSECOIJTA-DLEVMAFWSA-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

• 作为反应物：
  描述：

  乙酸酐 、 bis(β-D-glucopyranosyl)methane 在 吡啶 作用下， 生成 C-β,β-trehalose peracetate
  参考文献：
  名称：

  Ramberg-Bäcklund合成C键联二糖的方法。

  摘要：

  在Ramberg-Bäcklund重排中利用了现成的S-糖苷二氧化物来构建C键联的二糖。这种方法非常适合简单地通过烷基化剂的变化进行类似物合成，并且在此处通过β，β-C-海藻糖的合成（请参见反应方案），C-海藻糖的较高同源物和甲基C-龙胆生物苷进行说明。 。Bn ＝苄基。

  DOI：

  10.1002/(sici)1521-3773(19991004)38:19<2939::aid-anie2939>3.0.co;2-s
• 作为产物：
  描述：

  D-葡萄糖-二乙基缩硫醛 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 吡啶 、 potassium fluoride 、 无水碳酸镉 、 18-冠醚-6 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium methylate 、 乙酸酐 、 对甲苯磺酸 、 溶剂黄146 、 mercury dichloride 作用下， 以 甲醇 、 氯仿 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 51.0h， 生成 bis(β-D-glucopyranosyl)methane
  参考文献：
  名称：

  Synthesis and conformational studies of .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharides

  摘要：

  An expeditious methodology for the synthesis of beta-(1-->6)- and beta,beta-(1-->1)-linked C-disaccharides has been developed. The methodology is based on the fluoride ion-mediated coupling of the (base-stable) nitronate anion derived from a glycosylnitromethane (1) and an aldehydo-hexodialdose or -hexose derivative. The carba-analogs (methylene-bridged analogs) of beta-D-Glc-(1-->6)-D-Gal and of beta,beta-trehalose (beta-D-Glc-(1-->1)-beta-D-Glc) were thus obtained in six steps only from 1 and D-galactose-derived aldehyde 4 or aldehydo-D-glucose derivative 12, respectively. The preferred conformation of the (1-->1)-linked C-disaccharides, including the symmetrical C-beta,beta-trehalose, was established on the basis of the vicinal coupling constants about the interglycosidic C-C linkages. In all the compounds of this series, the beta-C-glycosidic linkages were found to adopt preferentially the ''anti'' conformation (C2-C1-C7-C1' torsional angle = approximately 180-degrees). Our studies revealed, in particular, that the solution conformation of C-beta,beta-trehalose, in which no stereoelectronic (exo-anomeric) effects are operating, is the same as the one predicted and determined for beta,beta-trehalose, thereby demonstrating that steric effects alone are sufficient to cause the greater stability of the preferred conformation of the parent disaccharide.

  DOI：

  10.1021/jo00053a033

文献信息

• A Ramberg−Bäcklund Approach to the Synthesis ofC-Glycosides,C-Linked Disaccharides, andC-Glycosyl Amino Acids
  作者：Duncan E. Paterson、Frank K. Griffin、Marie-Lyne Alcaraz、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1323::aid-ejoc1323>3.0.co;2-8

  日期：2002.4

  dioxides using the Meyers variant of the Ramberg−Backlund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg−Backlund rearrangement is also reported. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了使用 Ramberg-Backlund 重排的 Meyers 变体衍生自 S-糖苷二氧化物的外糖的合成应用。其中包括 β-糖苷酶抑制剂 12 的正式合成和生成螺环葡萄糖衍生物 17 和 18 的有效途径。 使用 Ramberg-Backlund 合成 C-连接的二糖 24、31 和 38 和 C-糖基氨基酸 49重排也有报道。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Ramberg-Bäcklund Approaches to the Synthesis of C-Linked Disaccharides
  作者：Frank K. Griffin、Duncan E. Paterson、Richard J. K. Taylor

  DOI：10.1002/(sici)1521-3773(19991004)38:19<2939::aid-anie2939>3.0.co;2-s

  日期：1999.10.4

  Readily available S-glycoside dioxides were utilized in a Ramberg-Bäcklund rearrangement for the construction of C-linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated here by the synthesis of beta,beta-C-trehalose (see reaction scheme), a higher homologue of C-trehalose, and methyl C-gentiobioside. Bn=benzyl.

  在Ramberg-Bäcklund重排中利用了现成的S-糖苷二氧化物来构建C键联的二糖。这种方法非常适合简单地通过烷基化剂的变化进行类似物合成，并且在此处通过β，β-C-海藻糖的合成（请参见反应方案），C-海藻糖的较高同源物和甲基C-龙胆生物苷进行说明。 。Bn ＝苄基。
• 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,
• Selective radical synthesis of β- C -disaccharides
  作者：Boris Vauzeilles、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(01)01533-7

  日期：2001.10

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.
• Synthesis and conformational studies of .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharides
  作者：Olivier R. Martin、Wen Lai

  DOI：10.1021/jo00053a033

  日期：1993.1

  An expeditious methodology for the synthesis of beta-(1-->6)- and beta,beta-(1-->1)-linked C-disaccharides has been developed. The methodology is based on the fluoride ion-mediated coupling of the (base-stable) nitronate anion derived from a glycosylnitromethane (1) and an aldehydo-hexodialdose or -hexose derivative. The carba-analogs (methylene-bridged analogs) of beta-D-Glc-(1-->6)-D-Gal and of beta,beta-trehalose (beta-D-Glc-(1-->1)-beta-D-Glc) were thus obtained in six steps only from 1 and D-galactose-derived aldehyde 4 or aldehydo-D-glucose derivative 12, respectively. The preferred conformation of the (1-->1)-linked C-disaccharides, including the symmetrical C-beta,beta-trehalose, was established on the basis of the vicinal coupling constants about the interglycosidic C-C linkages. In all the compounds of this series, the beta-C-glycosidic linkages were found to adopt preferentially the ''anti'' conformation (C2-C1-C7-C1' torsional angle = approximately 180-degrees). Our studies revealed, in particular, that the solution conformation of C-beta,beta-trehalose, in which no stereoelectronic (exo-anomeric) effects are operating, is the same as the one predicted and determined for beta,beta-trehalose, thereby demonstrating that steric effects alone are sufficient to cause the greater stability of the preferred conformation of the parent disaccharide.