Acetic acid (R)-1-((3aR,4R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-ethyl ester | 915215-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (R)-1-((3aR,4R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-ethyl ester
• CAS: 915215-00-8
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: YNAKWOZNLYNULH-ZHVGPZTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (R)-1-((3aR,4R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-ethyl ester 在 盐酸 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 61.0h， 生成 9-[(1'R,2'S,3'R,4'R)-2',3'-dihydroxy-4'-((1R)-1-hydroxyethyl)cyclopentyl]adenine
  参考文献：
  名称：

  5‘-Methylaristeromycin and Related Derivatives

  摘要：

  The biological versatility of aristeromycin (carbocyclic adenosine) is limited by accompanying cytotoxicity caused ostensibly by the intracellular formation of its 5'-nucleotide derivatives. Aristeromycin derivatives that offered steric interference to this transformation at the C-5' center were sought. This paper describes the facile stereospecific synthesis, where necessary, of such C-5'-methylated aristeromycin derivatives.

  DOI：

  10.1021/jo0612170
• 作为产物：
  描述：

  (3aS,4S,6R,6aR)-2,2-dimethyl-6-prop-1-en-2-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 N,N-diethylaniline borane 、 (S)-perhydropyrrolo[1,2-c][1,3,2]oxazaborole-based compound 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 17.5h， 生成 Acetic acid (R)-1-((3aR,4R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-ethyl ester
  参考文献：
  名称：

  5‘-Methylaristeromycin and Related Derivatives

  摘要：

  The biological versatility of aristeromycin (carbocyclic adenosine) is limited by accompanying cytotoxicity caused ostensibly by the intracellular formation of its 5'-nucleotide derivatives. Aristeromycin derivatives that offered steric interference to this transformation at the C-5' center were sought. This paper describes the facile stereospecific synthesis, where necessary, of such C-5'-methylated aristeromycin derivatives.

  DOI：

  10.1021/jo0612170