2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose

• 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: 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose
• 英文别名: (3R,4R,5S)-3,4,5-tris(phenylmethoxy)selenan-2-ol
• 化学式: C₂₆H₂₈O₄Se
• 分子量: 483.466
• InChiKey: RRTOLEHAULSGBX-NITSXXPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-核糖 在 sodium tetrahydroborate 、 samarium diiodide 、 氢气 、 mercury dichloride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 为溶剂， 反应 16.0h， 生成 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose
  参考文献：
  名称：

  Samarium(II) iodide mediated intramolecular homolytic substitution at selenium: Preparation of 5-seleno-D-pentopyranose sugars from common pentose starting materials

  摘要：

  Treatment of 2,3,4-tri-O-benzyl-5-benzylseleno-5-deoxyribose (9) with samarium(II) iodide in II-TF affords 2.3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose (10) in 50% isolated yield in a process most likely involving intramolecular homolytic substitution at the selenium atom. In a similar fashion, 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-xylopyranose (16) and 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-arabanopyranose (17) were prepared from analogous precursors in 21 and 12% yields respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00990-9

文献信息

• Preparation of 5-Selenopentopyranose Sugars from Pentose Starting Materials by Samarium(II) Iodide or (Phenylseleno)formate Mediated Ring Closures
  作者：Mathew A. Lucas、Oanh T.K. Nguyen、Carl H. Schiesser、Shi-Long Zheng

  DOI：10.1016/s0040-4020(00)00299-4

  日期：2000.6

  4-tri-O-benzyl-5-benzylseleno-d-arabit-1-yl formate (13, 21, 22) in transformations which involve intramolecular nucleophilic attack of the benzylseleno moiety with concomitant loss of carbon dioxide and phenylselenoate. In a complementary procedure, treatment of 2,3,4-tri-O-benzyl-5-benzylseleno-5-deoxyribose (19) with samarium(II) iodide in THF affords 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-d-ribopyranose

  2,3,4-三- ø -苄基-1,5-二去氧-5-硒代d-pentopyranose糖（16，23，24）很容易通过热制备的2,3,4-三ø -苄基-5--5-苄基硒代-d-ribit-1-基甲酸，2,3,4-三-O-苄基-5-苄基硒代-d-xylit-1-基甲酸根和2,3,4-三-O-苄基-5- benzylseleno-d-arabit -1-基甲酸盐（13，21，22），其中涉及benzylseleno部分与二氧化碳和phenylselenoate的同时损失分子内亲核进攻变换。在补充程序中，处理2,3,4-三-O-苄基-5-苄基硒基-5-脱氧核糖（19）在THF中用碘化sa（II）提供50％分离产率的2,3,4-三-O-苄基-5-脱氧-5-硒代-d-核吡喃糖（26），该过程最有可能涉及分子内均溶硒糖中硒原子上的取代。
• Samarium(II) iodide mediated intramolecular homolytic substitution at selenium: Preparation of 5-seleno-D-pentopyranose sugars from common pentose starting materials
  作者：Carl H. Schiesser、Shi-Long Zheng

  DOI：10.1016/s0040-4039(99)00990-9

  日期：1999.7

  Treatment of 2,3,4-tri-O-benzyl-5-benzylseleno-5-deoxyribose (9) with samarium(II) iodide in II-TF affords 2.3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose (10) in 50% isolated yield in a process most likely involving intramolecular homolytic substitution at the selenium atom. In a similar fashion, 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-xylopyranose (16) and 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-arabanopyranose (17) were prepared from analogous precursors in 21 and 12% yields respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.