Phenylmethoxymethylselanylbenzene | 1574563-61-3

• 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: Phenylmethoxymethylselanylbenzene
• CAS: 1574563-61-3
• 化学式: C₁₄H₁₄OSe
• 分子量: 277.225
• InChiKey: JZDLEPITAWSJLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Phenylmethoxymethylselanylbenzene 、 methyl (2S,4S,5R,6R)-5-acetamido-2-[(2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-acetyloxy-6-(acetyloxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到methyl (2S,4S,5R,6R)-5-acetamido-2-[(2R,3S,4S,5R,6S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-acetyloxy-6-(acetyloxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-6-phenylselanyloxan-4-yl]oxy-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  A facile method for synthesizing selenoglycosides based on selenium-transfer to glycosyl imidate

  摘要：

  A facile reaction for constructing selenoglycosides has been developed based on the transacetalization reaction between a selenoacetal and a glycosyl imidate. Glycosyl imidates were activated with TMSOTf to produce oxocarbenium ion, which reacted with benzyloxymethyl alkyl (aryl) selenide, providing alky (or aryl) selenoglycosides in high yields. Furthermore, this reaction was utilized in the synthesis of 2-(trimethylsilyl)ethylselenoglycoside, which, upon treatment with TBAF in the presence of an electrophile, was transformed into other selenoglycosides. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.151
• 作为产物：
  描述：

  苄基氯甲基醚 、 二苯基二硒醚 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.67h， 以77%的产率得到Phenylmethoxymethylselanylbenzene
  参考文献：
  名称：

  A facile method for synthesizing selenoglycosides based on selenium-transfer to glycosyl imidate

  摘要：

  A facile reaction for constructing selenoglycosides has been developed based on the transacetalization reaction between a selenoacetal and a glycosyl imidate. Glycosyl imidates were activated with TMSOTf to produce oxocarbenium ion, which reacted with benzyloxymethyl alkyl (aryl) selenide, providing alky (or aryl) selenoglycosides in high yields. Furthermore, this reaction was utilized in the synthesis of 2-(trimethylsilyl)ethylselenoglycoside, which, upon treatment with TBAF in the presence of an electrophile, was transformed into other selenoglycosides. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.151