| 1574563-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1574563-60-2
• 化学式: C₉H₁₂OSe
• 分子量: 215.154
• InChiKey: JCNCHQPDZCWYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  、 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87%的产率得到methyl (2R,4S,5R,6R)-4-acetyloxy-2-[[(2R,3S,4S,5R,6S)-3-acetyloxy-4,5-dibenzoyloxy-6-methylselanyloxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-(2,2,2-trichloroethoxycarbonylamino)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 、 二甲基二硒醚 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.67h， 以90%的产率得到
  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

文献信息

• Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing
  作者：Junpei Shimabukuro、Hisayoshi Makyio、Tatsuya Suzuki、Yosuke Nishikawa、Masato Kawasaki、Akihiro Imamura、Hideharu Ishida、Hiromune Ando、Ryuichi Kato、Makoto Kiso

  DOI：10.1016/j.bmc.2016.12.021

  日期：2017.2

  Selenium-incorporated fucoses (seleno-fucoses) differing in the position of the seleno-substituent were synthesized and applied to the X-ray structural determination of a carbohydrate-lectin complex using single/multi-wavelength anomalous dispersion (SAD/MAD) phasing. The hydroxyl groups at the C-1, -2, -3 and -4 position of fucose were individually substituted with a methylseleno group via a transacetalization reaction using MeSeCH2OBn or by an S(N)2 reaction with TolSe-equivalents to afford the corresponding MeSe-fucose. The three-dimensional structures of a fucose-binding lectin complexed with several of these MeSe-fucoses have been determined by SAD/MAD phasing by utilizing the diffraction of selenium in the bound MeSe-fucoses. (C) 2016 Elsevier Ltd. All rights reserved.