9-[(1R,2S,3S,4S)-2,3-O-isopropylidene-4-(methanesulfonyloxy)cyclopentan-1-yl]-9H-adenine | 263721-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(1R,2S,3S,4S)-2,3-O-isopropylidene-4-(methanesulfonyloxy)cyclopentan-1-yl]-9H-adenine
• 英文别名: [(3aS,4S,6R,6aS)-6-(6-aminopurin-9-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] methanesulfonate
• CAS: 263721-47-7
• 化学式: C₁₄H₁₉N₅O₅S
• 分子量: 369.401
• InChiKey: OLYKRVLALNPMLL-YKDSUIRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-[(1R,2S,3S,4S)-2,3-O-isopropylidene-4-(methanesulfonyloxy)cyclopentan-1-yl]-9H-adenine 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-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：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 在 二甲基亚砜 甲醇 、 4-二甲氨基吡啶 、 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 氨 、 水 、 sodium hydride 、 三乙胺 、 原甲酸三乙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 9-[(1R,2S,3S,4S)-2,3-O-isopropylidene-4-(methanesulfonyloxy)cyclopentan-1-yl]-9H-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

文献信息

• 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.