2',3',5'-tri-O-acetyl-4-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil | 1328937-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',5'-tri-O-acetyl-4-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil
• 英文别名: 2′,3′,5′-tri-O-acetyl-4′-C-p-toluenesulfonyloxymethylxylouridine；1-(4'-C-p-toluenesulfonyloxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl)uracil；[(2S,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-2-yl]methyl acetate
• CAS: 1328937-88-7
• 化学式: C₂₃H₂₆N₂O₁₂S
• 分子量: 554.532
• InChiKey: VUFVRMCVKWYLSX-FQOCKNPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-4-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil 在 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以92%的产率得到4'-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil
  参考文献：
  名称：

  新型C-4'-螺-氧杂环丁烷-α-L-核糖核苷的合成。

  摘要：

  从2'，3'，5'-三-O-乙酰基-4'-的合成，合成了新型C-4'-螺-氧杂环丁烷-α-L-核糖核苷T和U，总产率为39％和45％。 Cp-甲苯磺酰氧基甲基-β-D-木呋喃糖基胸腺嘧啶和2'，3'，5'-三-O-乙酰基-4'-Cp-甲苯磺酰氧基甲基-β-D-木呋喃糖基尿嘧啶。两种甲苯磺酸化的核苷前体均是根据最近开发的Novozyme®-435催化方法合成的。

  DOI：

  10.1016/j.carres.2017.04.018
• 作为产物：
  描述：

  [(3R,4R)-3,4,5-triacetyloxy-2-(acetyloxymethyl)oxolan-2-yl]methyl acetate 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 novozyme-435 作用下， 以 四氢呋喃 、 乙腈 、 正丁醇 为溶剂， 反应 22.0h， 生成 2',3',5'-tri-O-acetyl-4-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil
  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

• Enzymatic separation of epimeric 4-<i>C</i>-hydroxymethylated furanosugars: Synthesis of bicyclic nucleosides
  作者：Neha Rana、Manish Kumar、Vinod Khatri、Jyotirmoy Maity、Ashok K Prasad

  DOI：10.3762/bjoc.13.205

  日期：——

  Conversion of D-glucose to 4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose, which is a key precursor for the synthesis of different types of bicyclic/spiro nucleosides, led to the formation of an inseparable 1:1 mixture of the desired product and 4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-xylofuranose. A convenient environment friendly Novozyme®-435 catalyzed selective acetylation methodology

  D-葡萄糖向4-C-羟甲基-1,2-O-异亚丙基-α-D-呋喃呋喃糖的转化是合成不同类型的双环/螺核苷的关键前体，导致了不可分离的形成所需产物与4-C-羟甲基-1，2-O-异亚丙基-α-D-木呋喃糖的1∶1混合物。已开发出一种方便环境的Novozyme®-435催化的选择性乙酰化方法，用于定量定量分离核糖基和木三羟基呋喃糖苷的差向异构体混合物。单乙酰化差向异构体的结构，即通过酶促乙酰化获得的5-O-乙酰基-4-C-羟甲基-1,2-O-异亚丙基-α-D-核糖-和木呋喃糖的结构已经通过X-确认。射线研究其相应的4-Cp-甲苯磺酰氧基甲基衍生物。此外，