5-O-trityl-D-ribose diethyl dithioacetal | 108713-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-O-trityl-D-ribose diethyl dithioacetal
• 英文别名: O⁵-trityl-D-ribose-diethyldithioacetal；O⁵-Trityl-D-ribose-diaethyldithioacetal；(2R,3R,4R)-1,1-bis(ethylsulfanyl)-5-trityloxypentane-2,3,4-triol
• CAS: 108713-87-7
• 化学式: C₂₈H₃₄O₄S₂
• 分子量: 498.708
• InChiKey: CKEBMKMLRTUUMD-TWJOJJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-O-trityl-D-ribose diethyl dithioacetal 在 sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 为溶剂， 生成 2,3,4-tri-O-benzyl-5-benzylseleno-D-ribose diethyl dithioacetal
  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
• 作为产物：
  描述：

  D-核糖 生成 5-O-trityl-D-ribose diethyl dithioacetal
  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

• A NEW TRANSFORMATION OF ALDOSE DERIVED SYNTHONS TO PSEUDO-HEXOPYRANOSE OR PSEUDO-PENTOFURANOSE DERIVATIVES
  作者：Kin-ichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1246/cl.1986.1081

  日期：1986.7.5

  The d-ribose or d-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six- or five-membered carbocycle. Those carbocycles were converted into pseudo-β-l-mannopyranose derivatives or pseudo-β-l-arabinofuranose derivatives efficeintly.

  源自于d-核糖或d-赤藓糖的无环合成物，在C-1位拥有一个2-马隆基碳链，经过立体选择性环化形成了六元或五元碳环。这些碳环有效地转化为伪-β-l-甘露糖吡喃糖衍生物或伪-β-l-阿拉伯糖呋喃糖衍生物。
• Zinner, Chemische Berichte, 1953, vol. 86, p. 496,499
  作者：Zinner

  DOI：——

  日期：——
• A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1(hydroxymethyl)cyclopentane
  作者：Kinichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1021/jo00386a011

  日期：1987.5
• 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.