9-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine | 1328937-75-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine
• 英文别名: [(3R,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 1328937-75-2
• 化学式: C₁₉H₂₃N₅O₉
• 分子量: 465.42
• InChiKey: MLUZDQVEDYGORT-IIDMSEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  184
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  9-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine 在 novozyme-435 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 14.0h， 以82%的产率得到9-(4'-C-hydroxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Biocatalytic Deacylation Studies on Tetra-O-acyl-β-d-xylofuranosyl Nucleosides: Synthesis of xylo-LNA Monomers

  摘要：

  A Novozyme-435 catalytic methodology has been developed for selective deacylation of one of the acyloxy functions involving a primary -OH group over the other acyloxy functions involving primary and secondary -OH groups in 4'-C-acyloxymethyl-2',3',5'-tri-O-acyl-beta-D-xylofuranosyl nucleosides. Optimization of the biocatalytic reaction revealed that tetra-O-butanoyl-beta-D-xylofuranosyl nucleosides are the best substrates for the enzyme. The possibility of acyl migration during enzymatic deacylation reactions has been ruled out by carrying out biocatalytic deacylation reactions on mixed esters of 4'-C-hydroxymethyl-2',3',5'-tri-O-acetyl-beta-D-xylofuranosyl nucleosides. The developed methodology has been used for the efficient synthesis of xylo-LNA monomers T, U, A, and C in good yields.

  DOI：

  10.1021/jo201060t
• 作为产物：
  描述：

  4-C-acetoxymethyl-3,5-di-O-acetyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose 在 硫酸 、 四氯化锡 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 9-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Biocatalytic Deacylation Studies on Tetra-O-acyl-β-d-xylofuranosyl Nucleosides: Synthesis of xylo-LNA Monomers

  摘要：

  A Novozyme-435 catalytic methodology has been developed for selective deacylation of one of the acyloxy functions involving a primary -OH group over the other acyloxy functions involving primary and secondary -OH groups in 4'-C-acyloxymethyl-2',3',5'-tri-O-acyl-beta-D-xylofuranosyl nucleosides. Optimization of the biocatalytic reaction revealed that tetra-O-butanoyl-beta-D-xylofuranosyl nucleosides are the best substrates for the enzyme. The possibility of acyl migration during enzymatic deacylation reactions has been ruled out by carrying out biocatalytic deacylation reactions on mixed esters of 4'-C-hydroxymethyl-2',3',5'-tri-O-acetyl-beta-D-xylofuranosyl nucleosides. The developed methodology has been used for the efficient synthesis of xylo-LNA monomers T, U, A, and C in good yields.

  DOI：

  10.1021/jo201060t