9-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine | 137530-37-1

• 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-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine
• 英文别名: 5'-O-acetyl-3'-deoxyadenosine；5'-acetyl-3'-deoxyadenosine；5'-acetyl cordycepin；3'-deoxy-5'-O-acetyladenosine；[(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-2-yl]methyl acetate
• CAS: 137530-37-1
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: AIWPTOBJANGAJV-JOAULVNJSA-N

物化性质

• 沸点：
  593.7±60.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine 生成 虫草素
  参考文献：
  名称：

  Process for deoxygenating secondary alcohols

  摘要：

  将至少具有一个次级羟基且具有任何氨基保护的有机化合物中的次级羟基团从中去除的过程，包括将所述次级羟基团的反应性酯（所选自O-烷基硫酯和O-烷基硒酯组成的群）与至少一摩尔的有机锡氢化物（优选为三正丁基锡烷）在惰性、无极性溶剂中，在至少约100摄氏度的温度下，在惰性气氛下反应。该过程特别适用于去除氨基糖苷类抗生素中的次级醇，以产生具有抗菌活性的去氧衍生物。还描述了新颖的O-sec.-烷基硫代苯甲酸酯、O-sec.-烷基-S-甲基黄原酸酯、N-(sec.-烷氧硫代羰基)-咪唑酯和至少具有一个次级O-烷基基团的双O-烷基硫代碳酸酯，这些是所述过程的有用中间体。

  公开号：

  US04078139A1
• 作为产物：
  描述：

  乙酸乙烯酯 、 虫草素 在 CAL 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到9-(5-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine
  参考文献：
  名称：

  腺苷脱氨酶（EC 3.5.4.4。）对腺苷和脱氧腺苷乙酸酯的作用：5'-羟基对酶活性的关键作用

  摘要：

  从腺苷1，2'-脱氧腺苷3和3'-脱氧腺苷5个所有乙酸盐是由脂肪酶催化的反应制备。只有带有游离5'-羟基的乙酸盐才被腺苷脱氨酶（ADA）脱氨，这证实了5'-OH对酶活性的关键作用。

  DOI：

  10.1016/s0040-4020(00)00222-2

文献信息

• Method for production of nucleoside derivatives by selective hydrolysis
  申请人：Ajinomoto Co., Inc.

  公开号：US05310895A1

  公开（公告）日：1994-05-10

  A method for selective hydrolysis of nucleoside derivatives using cyclodextrin in basic solution is disclosed.

  本发明揭示了一种使用环糊精在碱性溶液中选择性水解核苷衍生物的方法。
• CONVENIENT SYNTHESIS OF FLUORINATED NUCLEOSIDES WITH PERFLUOROALKANESULFONYL FLUORIDES
  作者：Satoshi Takamatsu、Satoshi Katayama、Naoko Hirose、Etienne De Cock、Geert Schelkens、Marc Demillequand、Jozef Brepoels、Kunisuke Izawa

  DOI：10.1081/ncn-120016572

  日期：2002.12.31

  Perfluoroalkanesulfonyl fluorides are effective dehydroxy-fluorination agents for the hydroxyl group at the sugar moiety of nucleoside derivatives and give the corresponding fluorinated nucleosides in good yield with an inversion of configuration in a single step.
• A nucleoside derivative from Emericella nidulans
  作者：Nobuo Kawahara、Setsuko Sekita、Motoyoshi Satake、Shun-Ichi Udagawa

  DOI：10.1016/0031-9422(92)80302-u

  日期：1992.4

  5'-Acetyl-3'-deoxyadenosine, a new nucleoside derivative, has been isolated from Emericella nidulans var. lata, together with 3'-deoxyadenosine (cordycepin).
• An efficient enzymatic modification of cordycepin in ionic liquids under ultrasonic irradiation
  作者：Dan-Ni Zhang、Xiao-Yu Guo、Qiu-Huizi Yang、Zhi-Gang Chen、Li-Jia Tao

  DOI：10.1016/j.ultsonch.2014.02.023

  日期：2014.9

  A comparative study of the immobilized Candida antarctica lipase B (Novozym 435)-catalyzed acylation of cordycepin with vinyl acetate in ionic liquids (ILs) under ultrasonic irradiation and shaking was conducted. The application of ultrasonic irradiation instead of shaking during acylation resulted in an enhanced reaction rate and a higher level of substrate conversion. Among the various ILs examined, 1-butyl-3-methylimidazolium tetrafluorobrate ([C(4)MIm][BF4]) was the best medium for the reaction because it produced the highest substrate conversion. In [C(4)MIm][BF4], the optimal ultrasonic power, water activity, and reaction temperature were 120W, 0.33, and 50 degrees C, respectively. The acylation of cordycepin in [C(4)MIm][BF4] proved to be regioselective under both conditions: the C5'-OH was acylated. Novozym 435 exhibited a much higher operational stability in [C(4)MIm][BF4], and 58.0% of its original activity was maintained after ten reuse cycles under ultrasonic irradiation. Compared with the cordycepin, the rate of adenosine deaminase-catalyzed deamination was greatly reduced when the 5'-OH was substituted by acetyl group. These results demonstrated that the combined application of ultrasonic irradiation and IL as a medium was an efficient approach for the enzymatic modification of cordycepin. (C) 2014 Elsevier B.V. All rights reserved.
• JPS55149299A
  申请人：——

  公开号：JPS55149299A

  公开（公告）日：1980-11-20