2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine | 111556-91-3

• 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-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
• 英文别名: 2-Fluoro-3',5'-O-(1,1,3,3-tetraiso-propyl-disiloxane-1,3-diyl)adenosine；(6aR,8R,9R,9aS)-8-(6-amino-2-fluoropurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 111556-91-3
• 化学式: C₂₂H₃₈FN₅O₅Si₂
• 分子量: 527.744
• InChiKey: XOVUOFBCHCUOGH-QTQZEZTPSA-N

物化性质

• 沸点：
  606.2±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-fluoro-9-(2-chloro-2-deoxy-β-D-arabinofuranosyl)purin-6-amine
  参考文献：
  名称：

  Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine

  摘要：

  The synthesis of a series of 2-chloro- or 2-fluoro-9-(2-substituted-2-deoxy-beta-D-arabinofuranosyl)adenines (4g-n) is described. New compounds were prepared from either 2-chloroadenosine or 2-fluoroadenosine by first blocking the 3'- and 5'-hydroxyls as the tetraisopropyldisiloxane derivatives. Activation of O-2' by formation of a triflate followed by nucleophilic displacement allowed introduction of various groups in the proper configuration at C-2'. Fluoride ion treatment then produced the deblocked nucleosides. All of the new compounds were evaluated as cytotoxic agents against L1210 and H.Ep.-2 cells and as antiviral agents against herpes simplex viruses 1 and 2 and vaccinia virus in culture.

  DOI：

  10.1021/jm00397a024
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 2-氟腺苷 以 吡啶 、 甲苯 为溶剂， 以2.56 g (46%)的产率得到2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine
  参考文献：
  名称：

  Process for the preparation of fludarabine or fludarabine phosphate from

  摘要：

  提供一种用于生产氟达拉宾或氟达拉宾磷酸盐的方法，其中核苷酸鸟苷或适当衍生物被用作起始原料。鸟苷起始原料经历以下步骤：(a) 将6-酮基转化为6-氨基，(b) 将2-氨基转化为2-氟基，(c) 将核糖呋喃基转化为阿拉伯呋喃基。步骤(a)、(b)和(c)可以单独或同时进行，并且可以按任何顺序进行。

  公开号：

  US05602246A1

文献信息

• A Convenient Synthesis of 2′-Deoxy-2-fluoroadenosine; a Potential Prodrug for Suicide Gene Therapy
  作者：Abdalla E. A. Hassan、Anita T. Shortnacy-fowler、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257770008035007

  日期：2000.3

  A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 degrees C was found to affect an efficient deoxygenation to the corresponding 2'-deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.
• SECRIST, JOHN A.;SHORTNACY, ANITA T.;MONTGOMERY, JOHN A., J. MED. CHEM., 31,(1988) N 2, 405-410
  作者：SECRIST, JOHN A.、SHORTNACY, ANITA T.、MONTGOMERY, JOHN A.

  DOI：——

  日期：——
• Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine
  作者：John A. Secrist、Anita T. Shortnacy、John A. Montgomery

  DOI：10.1021/jm00397a024

  日期：1988.2

  The synthesis of a series of 2-chloro- or 2-fluoro-9-(2-substituted-2-deoxy-beta-D-arabinofuranosyl)adenines (4g-n) is described. New compounds were prepared from either 2-chloroadenosine or 2-fluoroadenosine by first blocking the 3'- and 5'-hydroxyls as the tetraisopropyldisiloxane derivatives. Activation of O-2' by formation of a triflate followed by nucleophilic displacement allowed introduction of various groups in the proper configuration at C-2'. Fluoride ion treatment then produced the deblocked nucleosides. All of the new compounds were evaluated as cytotoxic agents against L1210 and H.Ep.-2 cells and as antiviral agents against herpes simplex viruses 1 and 2 and vaccinia virus in culture.
• Process for the preparation of fludarabine or fludarabine phosphate from
  申请人：Schering Aktiengesellschaft

  公开号：US05602246A1

  公开（公告）日：1997-02-11

  A process for the production of fludarabine or fludarabine phosphate is provided, wherein the nucleoside guanosine or a suitable derivative is employed as the starting material. The guanosine starting material is subjected to (a) conversion of the 6-keto group into a 6-amino group, (b) conversion of the 2-amino group to a 2-fluoro group, and (c) conversion of the ribofuranosyl moiety to an arabinofuranosyl moiety. Steps (a), (b), and (c) can be performed individually or concomitantly and in any sequence.

  提供一种用于生产氟达拉宾或氟达拉宾磷酸盐的方法，其中核苷酸鸟苷或适当衍生物被用作起始原料。鸟苷起始原料经历以下步骤：(a) 将6-酮基转化为6-氨基，(b) 将2-氨基转化为2-氟基，(c) 将核糖呋喃基转化为阿拉伯呋喃基。步骤(a)、(b)和(c)可以单独或同时进行，并且可以按任何顺序进行。