2,3,4,5-tetra-O-acetyl-D-lyxose diethyl dithioacetal | 7241-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,5-tetra-O-acetyl-D-lyxose diethyl dithioacetal
• 英文别名: tetra-O-acetyl-aldehydo-D-lyxose-diethyldithioacetal；Tetra-O-acetyl-aldehydo-D-lyxose-diaethyldithioacetal；[(2R,3S,4S)-2,3,4-triacetyloxy-5,5-bis(ethylsulfanyl)pentyl] acetate
• CAS: 7241-19-2
• 化学式: C₁₇H₂₈O₈S₂
• 分子量: 424.537
• InChiKey: OGSWVSGRSHUBOP-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-lyxose diethyl dithioacetal 在 溴 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 8.0h， 生成 (1S)-2,3,4,5-tetra-O-acetyl-1-deoxy-1-S-ethyl-1-thio-1-(thymin-1-yl)-aldehydo-D-lyxose aldehydrol
  参考文献：
  名称：

  Synthesis of the four 1-(1-deoxy-d-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain

  摘要：

  Acetylated D-pentose diethyl dithioacetals were coupled by way of 1-bromo-1-ethylthio derivatives with 2,4-bis(trimethylsilyl)thymine to afford diastercomeric pairs of acyclic-sugar nucleoside analogues bearing a thymin-1-yl and an ethylthio group at C-1. Free-radical desulfurization by the action of tributylstannane removed the ethylthio group to afford the corresponding acetylated 1-(1-deoxy-D-pentitol-1-yl)thymines and subsequently the free title compounds in the arabino, lyxo, ribo, and xylo series. Conformations of the intermediates and products were studied in detail and the final products were evaluated for their potential as agents active against plant viruses and rice blast fungus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.12.003
• 作为产物：
  描述：

  D-来苏糖 在 吡啶 、 盐酸 作用下， 生成 2,3,4,5-tetra-O-acetyl-D-lyxose diethyl dithioacetal
  参考文献：
  名称：

  Acyclic Derivatives of d-Lyxose

  摘要：

  DOI：

  10.1021/ja01869a048

文献信息

• Zinner et al., Chemische Berichte, 1956, vol. 89, p. 800,804
  作者：Zinner et al.

  DOI：——

  日期：——
• Acyclic-sugar nucleoside analogs derived from cytosine with the d-aldopentoses, and from uracil with d-lyxose and d-ribose
  作者：Derek Horton、Satish S. Kokrady

  DOI：10.1016/s0008-6215(00)84880-6

  日期：1980.4