(3aR,4R,6S,6aS)-ethyl-4,5,6,6a-tetrahydro-6-hydroxy-2,2-dimethyl-3aH-cyclopenta-1,3-dioxole-4-acetate | 119906-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,6S,6aS)-ethyl-4,5,6,6a-tetrahydro-6-hydroxy-2,2-dimethyl-3aH-cyclopenta-1,3-dioxole-4-acetate
• 英文别名: ethyl 2-[(3aS,4S,6R,6aR)-4-hydroxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]acetate
• CAS: 119906-33-1
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: DWCAXWAYCKHRKA-MKHNBGRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6S,6aS)-ethyl-4,5,6,6a-tetrahydro-6-hydroxy-2,2-dimethyl-3aH-cyclopenta-1,3-dioxole-4-acetate 在 盐酸 、 偶氮二甲酸二异丙酯 、 氨 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (-)-5'-homoaristeromycin
  参考文献：
  名称：

  5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

  摘要：

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.019
• 作为产物：
  描述：

  在 potassium fluoride 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (3aR,4R,6S,6aS)-ethyl-4,5,6,6a-tetrahydro-6-hydroxy-2,2-dimethyl-3aH-cyclopenta-1,3-dioxole-4-acetate
  参考文献：
  名称：

  5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

  摘要：

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.019

文献信息

• Synthesis of carbocyclic nucleosides: preparation of (–)-5′-homoaristeromycin and analogues
  作者：Martin F. Jones、Stanley M. Roberts

  DOI：10.1039/p19880002927

  日期：——

  Optically pure 5′-homoaristeromycin has been prepared from (L)-ribonolactone using an intramolecular radical cyclisation process to form the five-membered carbocyclic ring with subsequent displacement of a triflate group using a substituted purine to introduce the base moiety.

  使用分子内自由基环化方法由（L）-核糖内酯制备光学纯的5'-同型阿霉素，以形成五元碳环，随后使用取代的嘌呤引入基础部分，将三氟甲磺酸酯基团置换。
• JONES, MARTIN F.;ROBERTS, STANLEY M., J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N1, C. 2927-2932
  作者：JONES, MARTIN F.、ROBERTS, STANLEY M.

  DOI：——

  日期：——