[5'-13C]pent-4-enyl 2;,3',5'-tri-O-benzoyl-α-D-erythropentofuranoside | 288851-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [5'-13C]pent-4-enyl 2;,3',5'-tri-O-benzoyl-α-D-erythropentofuranoside
• 英文别名: [(2R,3R,4R,5S)-3,4-dibenzoyloxy-5-pent-4-enoxyoxolan-2-yl](113C)methyl benzoate
• CAS: 288851-18-3
• 化学式: C₃₁H₃₀O₈
• 分子量: 531.563
• InChiKey: FLWSIATXYDZOKY-RNBUZUJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [5'-13C]pent-4-enyl 2;,3',5'-tri-O-benzoyl-α-D-erythropentofuranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.75h， 生成 腺苷-5'-13C
  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：

  苯甲酰氯 、 [5'-13C]pent-4-enyl D-erythropentofuranoside 在 吡啶 作用下， 反应 24.0h， 以70%的产率得到<5'-13C>pent-4-enyl 2',3',5'-tri-O-benzoyl-β-D-erythro-pentofuranoside
  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

• 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.