9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>adenine | 132235-76-8

• 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: 9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>adenine
• 英文别名: [(2S,3R,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl]methanol；[(2S,3R,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]methanol
• CAS: 132235-76-8
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: ROKFTZONUGKALY-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 5-O-benzoyl-3-C-<(benzoyloxy)methyl>-2,3-dideoxy-D-erythro-pentofuranoside 在 三甲基氯硅烷 、 叔丁基二甲硅基三氟甲磺酸酯 、 氨 、 氯化铵 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 44.0h， 生成 9-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV

  摘要：

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.

  DOI：

  10.1021/jo00009a012

文献信息

• The synthesis of novel 3′,5′-homocyclic nucleotides as potential anti-HIV agents
  作者：Michael G. B. Drew、Stephen Gorsuch、Jayne H. M. Gould、John Mann

  DOI：10.1039/a900800d

  日期：——

  (5S)-(5-tert-Butyldimethylsiloxymethyl)furan-2(5H)-one has been converted into cytosine 2′,3′-dideoxy-3′,5′-homocyclic monophosphate (and its 5-fluoro congener) together with an adenosine homocyclic monophosphate. These were designed as inhibitors of HIV reverse transcriptase although they did not possess such activity.

  (5S)-(5-叔丁基二甲基硅氧基甲基)呋喃-2(5H)-酮已被转化为胞苷2′,3′-二脱氧-3′,5′-同环单磷酸（及其5-氟同系物）和腺苷同环单磷酸。这些分子被设计为HIV逆转录酶的抑制剂，尽管它们并不具备此种活性。
• Synthesis and HIV Inhibition Activity of 2‘,3‘-Dideoxy-3‘-<i>C</i>-hydroxymethyl Nucleosides
  作者：E. Lee-Ruff、Mario Ostrowski、Azim Ladha、Dennis V. Stynes、Isaak Vernik、Ji-Long Jiang、Wei-Qin Wan、Shi-Fa Ding、Sadhna Joshi

  DOI：10.1021/jm950822k

  日期：1996.1.1

  A series if 2',3'-dideoxy-3'-C-hydroxymethyl purine nucleosides were prepared based on the photochemical ring expansion of a chiral cyclobutanone precursor, (2S)-trans-2,3-bis[(benzoyloxy)methyl]cyclobutanone, in the presence of a 6-substituted purine. Both alpha- and beta-anomers are produced in this transformation. Deprotection was effected by reaction of the photoadducts with saturated methanolic

  基于手性环丁酮前体（2S）-反式2,3-双[（苯甲酰氧基）甲基]的光化学扩环，制备了一系列2'，3'-二脱氧-3'-C-羟甲基嘌呤核苷环丁酮，在6-取代的嘌呤存在下。在这种转化中，α-和β-端基异构体均产生。通过光加合物与饱和甲醇氨的反应进行脱保护。测试了九种嘌呤核苷对HIV IIIB病毒对H9细胞的抑制作用。6-己氧基和腺嘌呤衍生物4e，c似乎在抑制病毒繁殖方面最有效，而4c的活性与ddI和AZT相当。
• SVANSSON, LARS;KVARNSTROM, INGEMAR;CLASSON, BJORN;SAMUELSSON, BERTIL, J. ORG. CHEM., 56,(1991) N, C. 2993-2997
  作者：SVANSSON, LARS、KVARNSTROM, INGEMAR、CLASSON, BJORN、SAMUELSSON, BERTIL

  DOI：——

  日期：——