4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal | 220931-02-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal
• CAS: 220931-02-2
• 化学式: C₃₅H₃₀O₆
• 分子量: 546.62
• InChiKey: SOAYUPAHBVLSIX-AWMDVYMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 ((2R,3R,4S,5S,6S)-3-(benzoyloxy)-5-iodo-6-methoxy-4-(2-oxo-1-phenylethoxy)tetrahydro-2H-pyran-2-yl)methyl benzoate
  参考文献：
  名称：

  The stereospecific synthesis of methyl α-C-mannobioside: a potential inhibitor of M. tuberculosis binding to human macrophages

  摘要：

  The synthesis of the C-glycoside analogue of the mycobacteria capping disaccharide, Man alpha 1-2Man, employing a glycosyl organosamarium is described.

  DOI：

  10.1039/cc9960001661
• 作为产物：
  描述：

  1-Chloro-1,3-diphenylprop-2-ene 在 吡啶 、 四丁基氟化铵 、 四丁基溴化铵 、 二正丁基氧化锡 作用下， 以 四氢呋喃 为溶剂， 生成 4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal
  参考文献：
  名称：

  The stereospecific synthesis of methyl α-C-mannobioside: a potential inhibitor of M. tuberculosis binding to human macrophages

  摘要：

  The synthesis of the C-glycoside analogue of the mycobacteria capping disaccharide, Man alpha 1-2Man, employing a glycosyl organosamarium is described.

  DOI：

  10.1039/cc9960001661

文献信息

• Samarium Diiodide PromotedC-Glycosylation: An Application to the Stereospecific Synthesis ofα-1,2-C-Mannobioside and Its Derivatives
  作者：Olivier Jarreton、Troels Skrydstrup、Juan-Félix Espinosa、Jesús Jiménez-Barbero、Jean-Marie Beau

  DOI：10.1002/(sici)1521-3765(19990201)5:2<430::aid-chem430>3.0.co;2-d

  日期：1999.2.1

  The synthesis of the C-glycoside analogue of the disaccharide Man(alpha 1-->2)Man has been achieved in a highly stereoselective and efficient manner employing an approach which closely parallels O-glycoside synthesis. The key step included the samarium diiodide reduction of mannosyl pyridylsulfone 18 in the presence of the C2-formyl branched mannoside derivative 17a to furnish the C-disaccharide derivative 19a in high yield. An intramolecular formyl group transfer reaction by means of 5-exo radical cyclization and concomitant fragmentation yielded aldehyde 17a stereospecifically. We also present a potentially viable alternative for the deoxygenation of sterically encumbered secondary alcohols. Attempts to extend this procedure to the synthesis of the C-trisaccharide of Man(alpha 1-->2)Man(alpha 1-->2)Man were frustrated by the inability of the disaccharide, pyridylsulfone derivative 43, to undergo coupling with carbonyl substrates upon treatment with SmI2, possibly owing to the sterically bulky C2 substituent.