(1'R,4'R)-9-(4'-hydroxycyclopent-2'-enyl)adenine | 158799-95-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'R,4'R)-9-(4'-hydroxycyclopent-2'-enyl)adenine
• 英文别名: (1R,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-ol
• CAS: 158799-95-2
• 化学式: C₁₀H₁₁N₅O
• 分子量: 217.23
• InChiKey: LBGHDVYWPMQKBS-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'R,4'R)-9-(4'-hydroxycyclopent-2'-enyl)adenine 在 三甲基溴硅烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1'R,4'R)-9-<4'-(phosphonomethoxy)cyclopent-2'-enyl>adenine
  参考文献：
  名称：

  立体合成碳环2'，3'-二脱氧-2'，3'-二氢-5'-芥子苷的四个立体异构体二膦酰基膦酸酯

  摘要：

  已经开发了从常见的对映体纯的烯丙基单乙酸酯3开始的四个立体异构对映体纯的5'-去碳环腺苷类似物4b，ent - 4b，5b和ent - 5b的灵活合成。将每个核苷类似物分别转化为相应的4'-膦酸酯，然后分别转化为二磷酸基膦酸酯4e，ent - 4e，5e和ent - 5e。

  DOI：

  10.1016/0040-4020(94)00986-5
• 作为产物：
  描述：

  (1R,3S)-(-)-1-乙酰氧基环戊烷-3-醇 在 四丁基氟化铵 、 氨 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 为溶剂， 生成 (1'R,4'R)-9-(4'-hydroxycyclopent-2'-enyl)adenine
  参考文献：
  名称：

  从一种常见的对映体纯的起始原料合成四种可能的立体异构5'-碳环核苷

  摘要：

  从常见的对映体纯的烯丙基单乙酸酯1开始，已开发出四种立体异构体对映体纯的5'-去碳环核苷2b，ent - 2b，3b和ent - 3b的灵活合成方法。

  DOI：

  10.1016/s0040-4039(00)73022-x

文献信息

• An efficient Mitsunobu coupling to adenine-derived carbocyclic nucleosides
  作者：Xue-qiang Yin、Wei-kuan Li、Stewart W. Schneller

  DOI：10.1016/j.tetlet.2006.10.126

  日期：2006.12

  Adenine is a poor substrate for the Mitsunobu process to carbocyclic nucleosides. However, N-6 amino bis-Boc-protected adenine is reported herein to undergo an efficient coupling under these conditions as a result of its increased solubility and the reduced competing nucteophilicity of the free adenine amino substituent. Products from this reaction are readily converted to aristeromycin, neplanocin, and analogs there from, including 5'-homoaristeromycin, a promising antiviral agent. (c) 2006 Published by Elsevier Ltd.
• 4′-Fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S-adenosyl-l-homocysteine hydrolase
  作者：Yukio Kitade、Takayuki Ando、Tsuyoshi Yamaguchi、Ayumi Hori、Masayuki Nakanishi、Yoshihito Ueno

  DOI：10.1016/j.bmc.2006.04.023

  日期：2006.8

  4 '-Fluorinated analogue of 9-[(1 ' R,2 ' S,3 ' R)-2 ',3 '-dihydroxy-eyelopentan-1 '-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(O) coupling conditions followed by fluorination with inversion of the configuration by using diethylammosulfur trifluoride, respectively. 4 '-P-Fluoro DHCaA and 2-amino-4 '-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.(c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Four Stereoisomers of Carbocyclic 5'-NOR D4A and Evaluation of Their Triphosphates as Substrates for DNA Polymerases
  作者：Natalia Dyatkina、Dniitry Semizarov、Lyubov Victorova、Alexander Krayevsky、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1080/15257779508012458

  日期：1995.5.1

  A method was developed for synthesis of the four stereoisomeric enantiomerically pure 5'-nor carbocyclic nucleosides 4b, ent-4b, 10 and ent-10 starting from the common enantiomerically pure allylic monoacetate 1. Nucleoside analogues were converted to the corresponding triphosphate derivatives 6, ent-6, 12, and ent-12. The substrate properties of the latters towards different DNA polymerases were evaluated.