3-nitrobenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside | 1258282-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-nitrobenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-5-iodo-6-[(3-nitrophenyl)methoxy]oxan-2-yl]methyl acetate
• CAS: 1258282-04-0
• 化学式: C₁₉H₂₂INO₁₀
• 分子量: 551.289
• InChiKey: OFFNGSDEPGJRMC-ZRSRNVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-硝基苯甲醇 、 乙酰化葡萄烯糖 在 ammonium cerium (IV) nitrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 13.5h， 以90%的产率得到3-nitrobenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside
  参考文献：
  名称：

  Convertible Formation of Different Glycoside Using Molecular Iodine

  摘要：

  The observation of convertible formation between 2-deoxy-2-iodo-O-glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation.

  DOI：

  10.3987/com-10-12043

文献信息

• An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of d-glucal using I2–Cu(OAc)2
  作者：Uthaiwan Sirion、Sittidate Purintawarrakun、Poolsak Sahakitpichan、Rungnapha Saeeng

  DOI：10.1016/j.carres.2010.08.020

  日期：2010.11

  An efficient and convenient method for the synthesis of 2-deoxy-2-iodo-O-glycosides from tri-O-acetyl-D-glucal with various alcohols by using I(2)-Cu(OAc)(2) is described. The 21 examples of corresponding glycosides were obtained in high yields, with good anomeric selectivity.

  描述了一种有效便捷的方法，可使用I（2）-Cu（OAc）（2）从三-O-乙酰基-D-葡萄糖与各种醇类合成2-脱氧-2-碘-O-糖苷。以高产率获得具有良好异头异构体选择性的21个相应糖苷实例。