3-methoxybenzyl 2-deoxy-2-iodo-3,4,6-tri-O-acetyl-α-D-glucopyranoside | 1258282-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxybenzyl 2-deoxy-2-iodo-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: 3-methoxybenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4-diacetyloxy-5-iodo-6-[(3-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate
• CAS: 1258282-05-1
• 化学式: C₂₀H₂₅IO₉
• 分子量: 536.318
• InChiKey: SMUTVLLNBLLPFH-IVDHNXQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲醇 、 3,4,6-tri-O-acetyl-D-glucal 在 碘 、 copper diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-methoxybenzyl 2-deoxy-2-iodo-3,4,6-tri-O-acetyl-α-D-glucopyranoside 、 3-methoxybenzyl 2-deoxy-2-iodo-3,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  一种通过使用I（2）-Cu（OAc）（2）对D-葡萄糖进行O-糖基化选择性合成2-deoxy-2-iodo-glycosides的有效方法。

  摘要：

  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。

  DOI：

  10.1016/j.carres.2010.08.020

文献信息

• Brønsted Acids of Anionic Chiral Cobalt(III) Complexes as Catalysts for the Iodoglycosylation or Iodocarboxylation of Glycals
  作者：Rui Wang、Wen-Qiang Wu、Na Li、Jia Shen、Kun Liu、Jie Yu

  DOI：10.1055/s-0037-1611810

  日期：2019.6

  Bronsted acids of anionic chiral Co(III) complexes were found to act as efficient phase-transfer catalysts for the diastereoselective iodoglycosylation or iodocarboxylation of glycals with a variety of alcohols or carboxylic acids, respectively, with N-iodosuccinimide as the iodo cation source. The corresponding 2-deoxy-2-iodoglycosides, including monosaccharides and disaccharides, and 2-deoxy-2-iodoglycosyl

  发现阴离子手性 Co(III) 配合物的布朗斯台德酸可作为有效的相转移催化剂，用于分别用各种醇或羧酸对糖醛进行非对映选择性碘糖基化或碘羧化，其中 N-碘代琥珀酰亚胺作为碘阳离子源。相应的 2-deoxy-2-iodoglycosides，包括单糖和二糖，以及 2-deoxy-2-iodoglycosyl 羧酸酯，它们具有很高的合成和生物学重要性，以高产率（高达 88%）获得，具有良好的非对映选择性（高达到 9:1 博士）。
• Convertible Formation of Different Glycoside Using Molecular Iodine
  作者：Rungnapha Saeeng、Uthaiwan Sirion、Yada Sirichan、Thanida Trakulsujaritchok、Poolsak Sahakitpichan

  DOI：10.3987/com-10-12043

  日期：——

  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.