1-(3-azido-2,3-dideoxy-β-L-threo-pentofuranosyl)thymine | 132979-41-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-azido-2,3-dideoxy-β-L-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2S,4S,5R)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 132979-41-0
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: HBOMLICNUCNMMY-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-azido-2,3-dideoxy-β-L-threo-pentofuranosyl)thymine 在 磷酸三甲酯 、 三正丁胺 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 生成 [[(2R,3S,5S)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
  参考文献：
  名称：

  New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities

  摘要：

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.

  DOI：

  10.1080/07328319708006190
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三(三甲基硅基)硅烷 、 二苯基磷酸 、 氨 、 一水合肼 、 溶剂黄146 、 三苯基膦 、 硫代氯甲酸苯酯 、 偶氮二甲酸二乙酯 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 1-(3-azido-2,3-dideoxy-β-L-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities

  摘要：

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.

  DOI：

  10.1080/07328319708006190

文献信息

• Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomers
  作者：Jesper Wengel、Jesper Lau、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1021/jo00011a026

  日期：1991.5

  We report the first synthesis of the L isomer of 3'-azido-3'-deoxythymidine (L-AZT). L-Arabinose was used as starting material for preparation of appropriately protected alpha,beta-unsaturated aldehyde 5. Michael-type addition of azide to 5 gave 3-azido-2,3-dideoxypentofuranoses 7 and 8 suitable for nucleoside coupling with silylated thymine to afford after deprotection L-AZT (11), 1-(3-azido,-2,3-dideoxy-alpha-L-erythro-pentofuranosyl)thymine (12), 1-(3-azido-2,3-dideoxy-beta-L-threo-pentofuranosyl)thymine (13) and 1-(3-azido-2,3-dideoxy-alpha-L-threo-pento-furanosyl)thymine (14). Anti-HIV activity of L-AZT is discussed.
• OSUMI, KENJI;SUGIMURA, HIDEYUKI, NOGUTI KEHNKYUDZE DZIXO,(1990) N3, S. 17-22
  作者：OSUMI, KENJI、SUGIMURA, HIDEYUKI

  DOI：——

  日期：——
• FLEET, GEORGE W. J.;SON, JONG CHAN;DEROME, ANDREW E., TETRAHEDRON, 44,(1988) N 2, 625-636
  作者：FLEET, GEORGE W. J.、SON, JONG CHAN、DEROME, ANDREW E.

  DOI：——

  日期：——
• New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities
  作者：G. Gosselin、V. Boudou、J.-F. Griffon、G. Pavia、C. Pierra、J.-L. Imbach、A.-M. Aubertin、R. F. Schinazi、A. Faraj、J.-P. Sommadossi

  DOI：10.1080/07328319708006190

  日期：1997.7

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.