3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate | 3396-72-3

• 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: 3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate
• 英文别名: 3-Desoxy-1,2-O-isopropyliden-5-O-tosyl-α-D-erythro-pentofuranose；1,2-O-isopropylidene-3-deoxy-5-O-(p-toluenesulfonyl)-D-xylose；[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 3396-72-3
• 化学式: C₁₅H₂₀O₆S
• 分子量: 328.386
• InChiKey: MOUTWRHBPQDLET-IACUBPJLSA-N

物化性质

• 沸点：
  447.0±30.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate 在 吡啶 、 18-冠醚-6 、 potassium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 137.0h， 生成 9-<(5R-cis)-5-(dimethoxymethyl)tetrahydrofuran-3-yl>-9H-purin-6-ylamine
  参考文献：
  名称：

  Zintek, Lawrence B.; Jeon, Geun Sook; Nair, Vasu, Heterocycles, 1994, vol. 37, # 3, p. 1853 - 1864

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 、 sodium methylate 、 N,N'-硫羰基二咪唑 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate
  参考文献：
  名称：

  Zintek, Lawrence B.; Jeon, Geun Sook; Nair, Vasu, Heterocycles, 1994, vol. 37, # 3, p. 1853 - 1864

  摘要：

  DOI：

文献信息

• Redlich, Hartmut; Schneider, Bernd, Liebigs Annalen der Chemie, 1983, # 3, p. 412 - 424
  作者：Redlich, Hartmut、Schneider, Bernd

  DOI：——

  日期：——
• Oshikawa, Tatsuo; Seo, Kuniaki; Yamashita, Mitsuji, Heterocyclic Communications, 2003, vol. 9, # 6, p. 559 - 566
  作者：Oshikawa, Tatsuo、Seo, Kuniaki、Yamashita, Mitsuji、Hanaya, Tadashi、Hamauzu, Yoshihiro、Yamamoto, Hiroshi

  DOI：——

  日期：——
• Synthesis and anti-HIV activity of isonucleosides
  作者：Donna M. Huryn、Barbara C. Sluboski、Steve Y. Tam、Manfred Weigele、Iain Sim、Barry D. Anderson、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00091a001

  日期：1992.6

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.
• Synthesis of iso-ddA, member of a novel class of anti-HIV agents
  作者：Donna M. Huryn、Barbara C. Sluboski、Steve Y. Tam、Louis J. Todaro、Manfred Weigele

  DOI：10.1016/s0040-4039(01)93867-5

  日期：1989.1
• Synthesis of Isomeric Dideoxynucleosides with Partial Symmetry
  作者：Vasu Nair、Lawrence Zintek、Geun Jeon

  DOI：10.1080/15257779508012391

  日期：1995.5.1

  Approaches to the synthesis of (S) and (R) enantiomers of hydroxymethylated isodideoxynucleosides have been developed. Because of the symmetry introduced at the carbon that normally bears the -CH2OH group, these compounds have only one asymmetric center and each enantiomeric series may be viewed as being both D- and L-related.