(-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-adenine | 153830-48-9

• 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: (-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-adenine
• 英文别名: 9-[(1R,2S,3R,4S)-4-hydroxy-2,3-O-isopropylidenecyclopentan-1-yl]-9H-adenine；2',3'-O-isopropylidenenoraristeromycin；(3aR,4S,6R,6aS)-6-(6-aminopurin-9-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 153830-48-9
• 化学式: C₁₃H₁₇N₅O₃
• 分子量: 291.31
• InChiKey: XBZFIPZCYFQULI-GOZTYBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-adenine 在 4-二甲氨基吡啶 、 叠氮化锂 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidenedioxy-4'-cyclopenten-1'-yl]-9-H-adenine
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x
• 作为产物：
  描述：

  (-)-β-(2'α,3'α-O-isopropylidenedioxy-4'β-trimethylacetoxycyclopent-1'-yl)-9-H-adenine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以76%的产率得到(-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-adenine
  参考文献：
  名称：

  快速的对映选择性合成具有抗衰老活性的碳环核苷

  摘要：

  描述了neplanocin A类似物1的简短合成，该类似物在亲本天然存在的碳环核苷的C-4处缺少羟亚甲基。此外，合成方案中的中间体无毒诺拉霉素3被证明具有良好的抗利什曼活性。

  DOI：

  10.1016/s0040-4039(00)61691-x

文献信息

• A Synthetic Approach to Carbocyclic Sinefungin
  作者：Adilson D. Da Silva、Edmilson JoseMaria、Pierre Blanchard、Jean-Louis Fourrey、Malka Robert-Gero

  DOI：10.1080/07328319808004308

  日期：1998.12

  An approach to an asymmetric synthesis of carbocyclic sinefungin (cSF) 2 is proposed. The sequence, which uses an original radical based chemistry for C-C bond formation, led to the immediate precursor 18 of the protected desired compound. While the overall yield is modest, it is noticeable that only a limited number of steps are needed to obtain the target compound.
• TROST, BARRY M.;KUO, GEE-HONG;BENNECHE, TORRE, J. AMER. CHEM. SOC., 110,(1988) N 2, 621-622
  作者：TROST, BARRY M.、KUO, GEE-HONG、BENNECHE, TORRE

  DOI：——

  日期：——
• Synthesis of 3′,4′-epoxynoraristeromycin analogs for molecular labeling probe of S-adenosyl-l-homocysteine hydrolase
  作者：Hiroharu Kojima、Atsushi Kozaki、Masafumi Iwata、Takayuki Ando、Yukio Kitade

  DOI：10.1016/j.bmc.2008.05.020

  日期：2008.7.1

  3',4'-Epoxynoraristeromycin analogs were designed and synthesized. Their affinities with human and Plasmodium falciparum S-adenosyl-L-homo-cysteine hydrolase were investigated. (c) 2008 Elsevier Ltd. All rights reserved.