bis(β-D-glucopyranosyl)nitromethane | 144791-37-7

• 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)nitromethane
• 英文别名: (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-[nitro-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]oxane-3,4,5-triol
• CAS: 144791-37-7
• 化学式: C₁₃H₂₃NO₁₂
• 分子量: 385.325
• InChiKey: QJVGSATYKKWHBS-PUPMPNESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  26
• 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：
  226
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis(β-D-glucopyranosyl)nitromethane 在 ammonium hydroxide 、 iron(II) sulfate 作用下， 以 水 为溶剂， 反应 0.33h， 以43%的产率得到(2S,3R,4R,5S,6R)-2-[amino-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  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
• 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 、 三氟化硼乙醚 、 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 、 乙腈 为溶剂， 反应 50.5h， 生成 bis(β-D-glucopyranosyl)nitromethane
  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 concise approach to .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharides. The synthesis of C-.beta.,.beta.-trehalose peracetate
  作者：Olivier R. Martin、Wen Lai

  DOI：10.1021/jo00305a004

  日期：1990.8
• 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.