Methyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside | 220931-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside
• CAS: 220931-03-3
• 化学式: C₃₆H₃₃IO₇
• 分子量: 704.558
• InChiKey: PCJLWTYVOIWGDZ-VWIDVAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Methyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside 在 samarium diiodide 、 偶氮二异丁腈 、 三正丁基氢锡 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.17h， 生成 Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Samarium Diiodide PromotedC-Glycosylation: An Application to the Stereospecific Synthesis ofα-1,2-C-Mannobioside and Its Derivatives

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<430::aid-chem430>3.0.co;2-d
• 作为产物：
  描述：

  1-Chloro-1,3-diphenylprop-2-ene 在 吡啶 、 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 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 、 乙腈 为溶剂， 生成 Methyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside
  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