(3aS)-3c-acetoxy-2t-acetoxymethyl-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one | 39687-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (3aS)-3c-acetoxy-2t-acetoxymethyl-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
• 英文别名: O^3'_,O5'-diacetyl-5-methyl-arabino-2,2'-anhydro-uridine；3',5'-Di-O-acetyl-2,2'-anhydrothymidin (IIb)；[(2R,4R,5R,6S)-5-acetyloxy-11-methyl-10-oxo-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-4-yl]methyl acetate
• CAS: 39687-10-0
• 化学式: C₁₄H₁₆N₂O₇
• 分子量: 324.29
• InChiKey: WDRNELGSTHRTBJ-HNCHTBHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(β-D-xylofuranosyl)-thymine 在 吡啶 、 碳酸二苯酯 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3aS)-3c-acetoxy-2t-acetoxymethyl-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
  参考文献：
  名称：

  Discovery of a novel route to β-thymidine: a precursor for anti-AIDS compounds

  摘要：

  介绍了一种从 D-木糖合成 δ-胸苷的新方法。

  DOI：

  10.1039/c39940001255

文献信息

• Diastereomeric 5,6-Dihydrothymidines. Preparation, Stereochemical Assignments, and MnO2 Oxidation Studies of Thymidines
  作者：Palle V. P. Pragnacharyulu、Chandra Vargeese、Michael Mc Gregor、Elie Abushanab

  DOI：10.1021/jo00115a026

  日期：1995.5

  A useful method for the stereospecific synthesis of beta-thymidine and beta-5,6-dihydrothymidine nucleosides is described. Condensation of methyl 2-formylpropionate and methyl methacrylate with oxazolines 8 furnished the corresponding 2,2'-anhydrothymidine 11 and a 2:1 diastereomeric mixture of 2,2'-anhydro-5,6-dihydrothymidine 10, respectively. While DDQ oxidation of 10 furnished 11, active MnO2 resulted in a selective dehydrogenation hitherto unreported in nucleoside chemistry. The minor diasteromer 10b was quantitatively converted to 11, leaving 10a unchanged. A plausible explanation for this selectivity was based on the stereochemistry at C5 which was determined by one-dimensional NOE studies.