<5'-13C>5'-chloro-5'-deoxyadenosine | 54447-58-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: <5'-13C>5'-chloro-5'-deoxyadenosine
• 英文别名: [5'-13C]5'-chloro-5'-deoxyadenosine；(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(chloro(113C)methyl)oxolane-3,4-diol
• CAS: 54447-58-4
• 化学式: C₁₀H₁₂ClN₅O₃
• 分子量: 286.679
• InChiKey: IYSNPOMTKFZDHZ-XUZOCFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  <5'-13C>5'-chloro-5'-deoxyadenosine 、 碘甲烷 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以71%的产率得到{[5'-13C]5'-chloro-5'-deoxyN1-methyladenosine⁺} iodide
  参考文献：
  名称：

  Synthesis of {[A15-13C]5?-deoxy-N1-methyladenosylcobalamin+}Cl?

  摘要：

  The synthesis of {[A15-C-13] 5'-deoxy-N1-methyladenosylcobalamin(+)}Cl-, an analog of coenzyme B-12, was accomplished by glycosidation of [5-C-13]D-ribose with 4-pentenol, followed by benzoylation, coupling to N-6-benzoylaminopurine, deprotection, chlorination at C5', methylation at N1, and oxidative addition to reduced cobalamin. The alpha and beta anomers of the intermediate pent-4-enyl-erythro-furanosides were detected and quantified for the first time.

  DOI：

  10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 六甲基磷酰三胺 、 N-碘代丁二酰亚胺 、 氯化亚砜 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 17.75h， 生成 <5'-13C>5'-chloro-5'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of {[A15-13C]5?-deoxy-N1-methyladenosylcobalamin+}Cl?

  摘要：

  The synthesis of {[A15-C-13] 5'-deoxy-N1-methyladenosylcobalamin(+)}Cl-, an analog of coenzyme B-12, was accomplished by glycosidation of [5-C-13]D-ribose with 4-pentenol, followed by benzoylation, coupling to N-6-benzoylaminopurine, deprotection, chlorination at C5', methylation at N1, and oxidative addition to reduced cobalamin. The alpha and beta anomers of the intermediate pent-4-enyl-erythro-furanosides were detected and quantified for the first time.

  DOI：

  10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c

文献信息

• A Convenient and Practical Synthesis of Coenzyme B₁₂Enriched in¹³C in the Cobalt-Bound Carbon
  作者：Shifa Cheng、Erie Zang、Kenneth L. Brown

  DOI：10.1080/00397919908086048

  日期：1999.3

  [A15-C-13]Adenosylcobalamin in which the labeled carbon is bound to the cobalt atom, and its analogs were synthesized from D-[5-C-13]ribose through anomeric hydroxyl activation, coupling with adenosines, and then alkylation of reduced B-12. The synthetic routes described here are mild, efficient, and proceed in reasonable yield.
• Synthesis of {[A15-13C]5?-deoxy-N1-methyladenosylcobalamin+}Cl?
  作者：Kenneth L. Brown、Zuping Xia

  DOI：10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c

  日期：2000.6

  The synthesis of [A15-C-13] 5'-deoxy-N1-methyladenosylcobalamin(+)}Cl-, an analog of coenzyme B-12, was accomplished by glycosidation of [5-C-13]D-ribose with 4-pentenol, followed by benzoylation, coupling to N-6-benzoylaminopurine, deprotection, chlorination at C5', methylation at N1, and oxidative addition to reduced cobalamin. The alpha and beta anomers of the intermediate pent-4-enyl-erythro-furanosides were detected and quantified for the first time.