((2R,3S,4R,5S,6S)-3-(benzoyloxy)-4-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6-hydroxytetrahydro-2H-pyran-2-yl)methyl benzoate | 220931-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((2R,3S,4R,5S,6S)-3-(benzoyloxy)-4-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6-hydroxytetrahydro-2H-pyran-2-yl)methyl benzoate
• CAS: 220931-22-6
• 化学式: C₄₄H₄₆O₈Si
• 分子量: 730.93
• InChiKey: UQODWWHYDAQBIQ-LJPXTOAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4R,5S,6S)-3-(benzoyloxy)-4-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6-hydroxytetrahydro-2H-pyran-2-yl)methyl benzoate 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal 在 吡啶 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 3 A molecular sieve 、 水 、 三正丁基氢锡 、 臭氧 、 三苯基膦 作用下， 以 乙腈 、 苯 为溶剂， 反应 16.17h， 生成 ((2R,3S,4R,5S,6S)-3-(benzoyloxy)-4-(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-6-hydroxytetrahydro-2H-pyran-2-yl)methyl benzoate
  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