9-(3-C-vinyl-β-D-xylopentofuranosyl)adenine | 162611-23-6

• 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-(3-C-vinyl-β-D-xylopentofuranosyl)adenine
• 英文别名: (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-ethenyl-2-(hydroxymethyl)oxolane-3,4-diol
• CAS: 162611-23-6
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: OZOLSDBTMCVGJI-ONUNSANNSA-N

物化性质

• 沸点：
  645.1±65.0 °C(predicted)
• 密度：
  1.77±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(3-C-vinyl-β-D-xylopentofuranosyl)adenine 在 sodium phosphate buffer 、 adenosine deaminase 作用下， 生成 9-((2R,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-4-vinyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  3'-β-乙炔基和2'-脱氧-3'-β-乙炔基腺苷：腺苷脱氨酶的第一个3'-β-支链腺苷底物。

  摘要：

  测试了3′-C-支链腺苷和2′-脱氧腺苷类似物1-7作为腺苷脱氨酶的底物。该酶将9-（3'-C-乙炔基-β-D-核糖-戊呋喃糖基）腺嘌呤1及其2'-脱氧类似物7脱氨，而乙烯基和乙基衍生物2和3没有。通过脱氨酶将9-（3'-C-支链的β-D-二甲苯基-呋喃呋喃糖基）腺嘌呤4-6脱氨基。

  DOI：

  10.1016/s0960-894x(99)00639-3
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 9-(3-C-vinyl-β-D-xylopentofuranosyl)adenine
  参考文献：
  名称：

  Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides

  摘要：

  In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).

  DOI：

  10.1016/0040-4039(94)02434-d

文献信息

• Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides
  作者：Pierre M.J Jung、Alain Burger、Jean-Francois Biellmann

  DOI：10.1016/0040-4039(94)02434-d

  日期：1995.2

  In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).
• 3′-β-ethynyl and 2′-deoxy-3′-β-ethynyl adenosines: first 3′-β-branched-adenosines substrates of adenosine deaminase
  作者：Denis Tritsch、Pierre M.J. Jung、Alain Burger、Jean-François Biellmann

  DOI：10.1016/s0960-894x(99)00639-3

  日期：2000.1

  The 3'-C-branched-adenosine and 2'-deoxyadenosine analogues 1-7 were tested as substrate of adenosine deaminase. The 9-(3'-C-ethynyl-beta-D-ribo-pentofuranosyl)adenine 1 and its 2'-deoxy analogue 7 were deaminated by the enzyme while the vinyl and ethyl derivatives 2 and 3 were not. The 9-(3'-C-branched-beta-D-xylo-pentofuranosyl)adenines 4-6 were deaminated by the deaminase.

  测试了3′-C-支链腺苷和2′-脱氧腺苷类似物1-7作为腺苷脱氨酶的底物。该酶将9-（3'-C-乙炔基-β-D-核糖-戊呋喃糖基）腺嘌呤1及其2'-脱氧类似物7脱氨，而乙烯基和乙基衍生物2和3没有。通过脱氨酶将9-（3'-C-支链的β-D-二甲苯基-呋喃呋喃糖基）腺嘌呤4-6脱氨基。