cyclohexyl-3,4,6-O-benzyl-2-deoxy-2-iodo-α-D-glucoside | 84207-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl-3,4,6-O-benzyl-2-deoxy-2-iodo-α-D-glucoside
• 英文别名: cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside；cyclohexyl 2-deoxy-2-iodo-3,4,6-tri-O-benzyl-α-D-glucopyranoside；(2S,3S,4S,5R,6R)-2-cyclohexyloxy-3-iodo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 84207-52-3
• 化学式: C₃₃H₃₉IO₅
• 分子量: 642.574
• InChiKey: CXOILHDRHXZFOF-GGJJTXTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃阿拉伯糖 在 N-碘代丁二酰亚胺 、 正丁基锂 、 三氟甲磺酸 、 4 A molecular sieve 、 potassium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 cyclohexyl-3,4,6-O-benzyl-2-deoxy-2-iodo-α-D-glucoside
  参考文献：
  名称：

  Phenyl 2-Deoxy-2-iodo-1-thio-glycosides: New Glycosyl Donors for the Stereoselective Synthesis of 2-Deoxy-oligosaccharides

  摘要：

  通过烯化和碘诱导的环化反应，由简单戊糖制备的苯基2-脱氧-2-碘-1-硫代糖苷已被证明是立体选择性合成2-脱氧-2-碘寡糖的有效糖供体，这些寡糖是2-脱氧寡糖的前体。

  DOI：

  10.1055/s-2003-42066

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）。
• HIGHLY STEREOSELECTIVE SYNTHESIS OF α-D-GLUCOPYRANOSIDES BY THE<i>N</i>-IODOSUCCINIMIDE-PROMOTED INTERNAL CYCLIZATION
  作者：Keisuke Suzuki、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.1525

  日期：1982.10.5

  Highly stereoselective cyclizations of hydroxy enol ethers are effected by N-iodosuccinimide to result in the exclusive formation of 2′-deoxy-2′-iodo-α-d-glucopyranosides. An analog of glycolipid is also successfully synthesized according to the present method.

  N-碘代丁二酰亚胺可高效地使羟基烯醇醚发生立体选择性环化反应，从而形成独特的2′-脱氧-2′-碘-α-d-吡喃葡萄糖苷。根据现有方法，还成功合成了类似糖脂。
• Glycosylations of Glycals using <i>N</i>-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides
  作者：Tomoya Kimura、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.joc.5b01542

  日期：2015.10.2

  The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)(3) were effectively realized to give the corresponding 2-deoxyglycosides in high yields.