methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside | 676598-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside
• 英文别名: methyl 5-O-p-toluoyl-2-deoxy-D-ribofuranoside；[(2R,3S)-3-hydroxy-5-methoxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 676598-19-9
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: NIDKHKUHGRYQFG-LAGVYOHYSA-N

物化性质

• 沸点：
  414.9±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside 在 吡啶 盐酸 、 四氯化锡 、 溶剂黄146 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 乙醚 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 39.83h， 生成 1-<3-O-benzyl-2-deoxy-5-O-(4-methylbenzoyl)-α-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Stereochemical control as a function of protecting-group participation in 2-deoxy-D-erythro-pentofuranosyl nucleosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)85610-4
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 甲基-2-脱氧-D-核糖 以 吡啶 为溶剂， 反应 18.0h， 以51%的产率得到methyl 2-deoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside
  参考文献：
  名称：

  Stereochemical control as a function of protecting-group participation in 2-deoxy-D-erythro-pentofuranosyl nucleosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)85610-4

文献信息

• Synthesis and DNA/RNA Binding Properties of Conformationally Constrained Pyrrolidinyl PNA with a Tetrahydrofuran Backbone Deriving from Deoxyribose
  作者：Pitchanun Sriwarom、Panuwat Padungros、Tirayut Vilaivan

  DOI：10.1021/acs.joc.5b00890

  日期：2015.7.17

  following an 11-step reaction sequence. The tetrahydrofuran amino acid is used as a building block for a new peptide nucleic acid (PNA), which exhibits excellent DNA binding affinity with high specificity. It also shows preference for binding to DNA over RNA and specifically in the antiparallel orientation. In addition, the presence of the hydrophilic tetrahydrofuran ring in the PNA structure reduces nonspecific

  糖衍生的环状β-氨基酸是设计折叠剂和其他仿生结构的重要组成部分。我们在此报告了C活化的N - Fmoc保护的反式-（2 S，3 S）-3-氨基四氢呋喃-2-羧酸的首次合成，作为Fmoc固相肽合成的基础。从2-deoxy- d开始-核糖，按照11步反应顺序，以6.7％的总收率获得产物。四氢呋喃氨基酸用作新肽核酸（PNA）的构件，该肽核酸具有出色的DNA结合亲和力和高特异性。它还显示了与DNA结合的优先于RNA的结合，特别是在反平行方向上。另外，在PNA结构中亲水四氢呋喃环的存在减少了非特异性相互作用和自聚集，这由于其疏水性而在PNA中是一个普遍的问题。
• Synthesis, Structure−Activity Relationships, and Mechanism of Drug Resistance of <scp>d</scp>- and <scp>l</scp>-β-3‘-Fluoro-2‘,3‘-unsaturated-4‘-thionucleosides as Anti-HIV Agents
  作者：Wei Zhu、Youhoon Chong、Hyunah Choo、Judy Mathews、Raymond F. Schinazi、Chung K. Chu

  DOI：10.1021/jm0303148

  日期：2004.3.1

  Various D- and L-2',3'-unsaturated 3'-fluoro-4'-thionucleosides (D- and L-3'F-4'Sd4Ns) were synthesized for the studies of structure-activity relationships. The synthesized D-2',3'-unsaturated 3'-fluoro-4'-thionucleosides did not show any significant antiviral activity against HIV-1, while unnatural L-nucleosides such as cytosine 34 (EC50 = 0.13 muM; EC90 = 1.7 muM) and 5-fluorocytosine 35 (EC50 = 0.031 muM; EC90 = 0.35 muM) derivatives exhibited potent antiHIV activity without significant toxicity. Molecular modeling study shows that the X-fluorine atom of the D-2',3'-unsaturated cytidine triphosphate (D-3'F-4'Sd4CTP) experiences unfavorable electrostatic interaction with its own triphosphate moiety, resulting in the decreased binding affinity to wild-type HIV-1 reverse transcriptase (RT), which may be one of the reasons for the insensitivity of HIV-1 RT to these compounds. On the other hand, L-3'F-4'Sd4CTP binds to the active site of wild-type HIV-1 RT without steric hindrance and there is a possible hydrogen bonding between the X-fluorine atom and Asp185, which correlates with its potent anti-HIV activity. However, L-3'F-4'Sd4C 34 and L-3'F-4'Sd4FC 35 showed high cross-resistance to 3TC-resistant mutant (M184V) RT. Like other unnatural L-nucleosides, the unfavorable steric hindrance of the sugar moiety Of L-3'F-4'Sd4CTP with the side chain of Val184 explains its significant cross-resistance to the M184V mutant.