1-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)thymine | 1067169-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)thymine
• 英文别名: [(3R,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1067169-92-9
• 化学式: C₁₉H₂₄N₂O₁₁
• 分子量: 456.406
• InChiKey: MFUXGGBMSRXXJN-BFYDXBDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)thymine 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以93%的产率得到1-(4'-C-hydroxymethyl-β-D-xylofuranosyl)thymine
  参考文献：
  名称：

  化学酶促合成3'-O，4'-C-亚甲基连接的[小α] -L-阿拉伯糖核苷

  摘要：

  脂酶[注册标志] TL IM使用乙酸乙烯酯作为乙酰基供体，催化C-4'-羟甲基在C-4'-羟甲基-[小β] -D-木呋喃糖基核苷的其他三个羟基上的非对映选择性乙酰化。相应的C-4'-乙酰氧基甲基核苷

  DOI：

  10.1039/c6ra17218k
• 作为产物：
  描述：

  4-C-(hydroxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-(4'-C-acetoxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)thymine
  参考文献：
  名称：

  化学酶促合成3'-O，4'-C-亚甲基连接的[小α] -L-阿拉伯糖核苷

  摘要：

  脂酶[注册标志] TL IM使用乙酸乙烯酯作为乙酰基供体，催化C-4'-羟甲基在C-4'-羟甲基-[小β] -D-木呋喃糖基核苷的其他三个羟基上的非对映选择性乙酰化。相应的C-4'-乙酰氧基甲基核苷

  DOI：

  10.1039/c6ra17218k

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.
• Biocatalytic Deacylation Studies on Tetra-<i>O</i>-acyl-β-<scp>d</scp>-<i>xylo</i>furanosyl Nucleosides: Synthesis of <i>xylo</i>-LNA Monomers
  作者：Sunil K. Singh、Vivek K. Sharma、Kapil Bohra、Carl E. Olsen、Ashok K. Prasad

  DOI：10.1021/jo201060t

  日期：2011.9.16

  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.