(1S,3R,4R,7R)-3-(adenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane | 673456-40-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (1S,3R,4R,7R)-3-(adenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 9-(2'O,4'C-methylene-β-D-xylofuranosyl)adenine；(1S,3R,4R,7R)-3-(adenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2:2:1]heptane；(1S,3R,4R,7S)-3-(adenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane；(1S,3R,4R,7R)-3-(6-aminopurin-9-yl)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-7-ol
• CAS: 673456-40-1
• 化学式: C₁₁H₁₃N₅O₄
• 分子量: 279.255
• InChiKey: GHKDRNDFVCEETA-CCXSFMJYSA-N

物化性质

• 熔点：
  236-238 °C
• 沸点：
  660.0±65.0 °C(Predicted)
• 密度：
  2.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl methoxyalaninyl phosphorochloridate 、 (1S,3R,4R,7R)-3-(adenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 在 吡啶 、 叔丁基氯化镁 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 48.0h， 生成 phenyl-[methoxy-L-alaninyl]-[((1R,3R,4R,7S)-3-(adenine-9-yl)-7-hydroxy-2,5-dioxabicyclo[2:2:1]heptane-1-yl)methyl] phosphate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of LNA Phosphoramidates

  摘要：

  The synthesis of LNA phosphoramidates is presented. The LNA phosphoramidates were evaluated for their ability to inhibit cell proliferation of the human prostate cancer cell line 15PC3. A number of the LNA phosphoramidates showed cell proliferation inhibition determined by the MTS assay.

  DOI：

  10.1080/15257770701571834
• 作为产物：
  描述：

  9-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine 在 吡啶 、 novozyme-435 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正丁醇 为溶剂， 反应 32.0h， 生成 (1S,3R,4R,7R)-3-(adenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Biocatalytic Deacylation Studies on Tetra-O-acyl-β-d-xylofuranosyl Nucleosides: Synthesis of xylo-LNA Monomers

  摘要：

  A Novozyme-435 catalytic methodology has been developed for selective deacylation of one of the acyloxy functions involving a primary -OH group over the other acyloxy functions involving primary and secondary -OH groups in 4'-C-acyloxymethyl-2',3',5'-tri-O-acyl-beta-D-xylofuranosyl nucleosides. Optimization of the biocatalytic reaction revealed that tetra-O-butanoyl-beta-D-xylofuranosyl nucleosides are the best substrates for the enzyme. The possibility of acyl migration during enzymatic deacylation reactions has been ruled out by carrying out biocatalytic deacylation reactions on mixed esters of 4'-C-hydroxymethyl-2',3',5'-tri-O-acetyl-beta-D-xylofuranosyl nucleosides. The developed methodology has been used for the efficient synthesis of xylo-LNA monomers T, U, A, and C in good yields.

  DOI：

  10.1021/jo201060t

文献信息

• Synthesis of a Base-Protected<i>xylo</i>-LNA Adenine Nucleoside
  作者：Torsten Bryld、Jesper Wengel

  DOI：10.1081/ncn-120022826

  日期：2003.10

  Synthesis of (1S,3R,4R,7R)-7-hydroxy-1-hydroxymethyl-3-(6-N-benzoyl-adenin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (2), a base-protected xylo-LNA adenine nucleoside, has been accomplished using a convergent synthetic strategy starting from 1,2-di-O-acetylfuranose 3.

  （1S，3R，4R，7R）-7-羟基-1-羟甲基-3-（6-N-苯甲酰基-腺嘌呤-9-基）-2,5-二氧杂双环[2.2.1]庚烷的合成（2） ，是一种从1,2-二-O-乙酰基呋喃糖3开始的聚合合成策略，可完成一种碱基保护的xylo-LNA腺嘌呤核苷。
• LNA NUCLEOSIDE PHOSPHORAMIDATES
  申请人：Santaris Pharma A/S

  公开号：EP2099461B1

  公开（公告）日：2012-03-28