1-(4'-C-hydroxymethyl-2',3',5'-tri-O-butanoyl-β-D-xylofuranosyl)thymine | 1067169-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4'-C-hydroxymethyl-2',3',5'-tri-O-butanoyl-β-D-xylofuranosyl)thymine
• CAS: 1067169-99-6
• 化学式: C₂₃H₃₄N₂O₁₀
• 分子量: 498.53
• InChiKey: GMCSFUJTQGDQAC-LUBSMZHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  163.22
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(4'-C-hydroxymethyl-2',3',5'-tri-O-butanoyl-β-D-xylofuranosyl)thymine 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 10.0h， 以93%的产率得到[(2S,3R,4R,5R)-3,4-di(butanoyloxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-2-yl]methyl butanoate
  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：

  1-(4'-C-hydroxymethyl-β-D-xylofuranosyl)thymine 在 吡啶 、 novozyme-435 作用下， 以 四氢呋喃 、 二氯甲烷 、 正丁醇 为溶剂， 反应 8.0h， 生成 1-(4'-C-hydroxymethyl-2',3',5'-tri-O-butanoyl-β-D-xylofuranosyl)thymine
  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

文献信息

• Novel Selective Biocatalytic Deacylation Studies on Key Precursors for Bicyclonucleosides
  作者：Ashok K. Prasad、Sunil K. Singh、Neerja Kalra、Nidhi Singhal、Jesper Wengel、Virinder S. Parmar

  DOI：10.1080/15257770701544302

  日期：2007.11.26

  Immobilized Candida antarctica lipase and Thermomyces lanuginosus lipase catalyze the deacylation of precursors of LNA analogs, 4'-C-acyloxymethyl-2',3',5'-tri-O-acyl-beta-L-threopentofuranosylthymine and 4-C-acyloxymethyl-3,5-di-O-acyl-1,2-O-(1-methylethylidene)-beta-L-threopentofuranose, respectively in a highly selective and efficient manner.