2',3'-O-ethoxymethyleneadenosine | 3250-02-0

• 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: 2',3'-O-ethoxymethyleneadenosine
• 英文别名: 2',3'-O-ethoxymethylidene adenosine；O^2',O^3'-Aethoxymethylen-adenosin；2',3'-O-Ethoxymethylenadenosin；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2-ethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 3250-02-0
• 化学式: C₁₃H₁₇N₅O₅
• 分子量: 323.308
• InChiKey: GSAINKDJWMWPIU-ANYBFRSCSA-N

物化性质

• 熔点：
  228-230 °C(Solv: ethanol (64-17-5))
• 沸点：
  604.4±65.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2',3'-O-ethoxymethyleneadenosine 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 为溶剂， 25.0~50.0 ℃ 、405.3 kPa 条件下， 反应 106.0h， 生成 5'-deoxy-5'-adenosineacetic acid
  参考文献：
  名称：

  Kurihara, Takushi; Ota, Atsutoshi; Hayashi, Hirofumi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 2126 - 2129

  摘要：

  DOI：

文献信息

• A Stepwise one-pot synthesis of arylN-phosphonamidothionate derivatives of nucleosides
  作者：Zhi-Wei Miao、Hua Fu、Guang-Zhong Tu、Ji-Gang Zhu、Hui-Wang Ai、Yu-Fen Zhao

  DOI：10.1002/hc.10080

  日期：——

  Novel aryl N-phosphonamidothionate derivatives of nucleosides as membrane-soluble prodrugs of bioactive free nucleotides have been prepared by phosphochloridothioate chemistry. Unprotected nucleosides, for example uridine and adenosine, were used; phosphorylation took place selectively at the 5′-position. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:62–66, 2003; Published online in Wiley InterScience

  已通过硫代磷酸氯化学制备了作为生物活性游离核苷酸的膜可溶性前药的核苷的新型芳基 N-硫代膦酰胺衍生物。使用未保护的核苷，例如尿苷和腺苷；磷酸化选择性地发生在 5' 位。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:62–66, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10080
• Application of Wittig Reaction to Adenosine Derivatives
  作者：Zhang Jun-Dong、Zhang Li-He

  DOI：10.1055/s-1990-27050

  日期：——

  2′,3′-O-Ethoxymethyleneadenosine 5′-aldehyde (3)was reacted with Wittig reagents 4 and 5 to give the corresponding α,β- unsaturated adenosine esters 6 and 7. The dehydrated compounds 9 and 10 were separated from this reaction and inversion of configuration at C-3′ in ribofuranoside was observed.

  2′,3′-O-乙氧基亚甲基腺苷 5′-醛（3）与维蒂希试剂 4 和 5 反应，得到相应的δ,δ²- 不饱和腺苷酯 6 和 7。从这一反应中分离出脱水化合物 9 和 10，并观察到呋喃核糖苷中 C-3′ 处的构型反转。
• Holy, Antonin; Rosenberg, Ivan, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 12, p. 3447 - 3463
  作者：Holy, Antonin、Rosenberg, Ivan

  DOI：——

  日期：——
• Aminoacyl derivatives of nucleosides, nucleotides and polynucleotides. Part 35. Synthesis of 2'(3')-O-aminoacyl triribonucleoside diphosphates using the triester method
  作者：Gyanendra Kumar、Lech Celewicz、Stanislav Chladek

  DOI：10.1021/jo00343a007

  日期：1982.2
• ONE POT SYNTHESIS OF NUCLEOSIDE 5′-THIOPHOSPHORAMIDATES
  作者：Zhi-Wei Miao、Hua Fu、Bo Han、Yu-Fen Zhao

  DOI：10.1081/scc-120003155

  日期：2002.1

  Nucleoside 5 -thiophosphoramidates were synthesized through a highly efficient approach; i.e., thiophosphoryl chloride was sequentially treated with an amino acid methyl ester and a protected or unprotected nucleoside. The product was then hydrolyzed in 2 M NH4OH.