5-Methoxymethyl-3',5'-di-O-acetyl-2'-deoxyuridine | 129580-08-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-Methoxymethyl-3',5'-di-O-acetyl-2'-deoxyuridine
• 英文别名: 3',5'-di-O-acetyl-5-(methoxymethyl)-2'-deoxyuridine；[(2R,3S,5R)-3-acetyloxy-5-[5-(methoxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 129580-08-1
• 化学式: C₁₅H₂₀N₂O₈
• 分子量: 356.332
• InChiKey: CBAGYEWQVUGNDK-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.53
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-Methoxymethyl-3',5'-di-O-acetyl-2'-deoxyuridine 在 氨 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 35.0h， 生成 N⁴-hydroxy-5-methoxymethyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis, Conformation, and Antiviral Activity of 5-Methoxymethyl-2′-deoxycytidine Analogs

  摘要：

  Analogs of 5-methoxymethyl-2'-deoxycytidine, MMdCyd (1) by substitution at N-4 were, synthesized to impart resistance against deamination. The anti HSV-1 activity and solution conformation of analogs' were determined. N-4-Butanoyl-MMdCyd (10) was a potent inhibitor of HSV-1 replication while N-4-hexanoyl-MMdCyd (11), N-4-propanoyl-MMdCyd(9) and N-4-acetyl-MMdCyd (8) had good activity against HSV-1 replication. All other analogs were devoid of activity against HSV-1.

  DOI：

  10.1081/ncn-120019532
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium hydrogencarbonate 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 5-Methoxymethyl-3',5'-di-O-acetyl-2'-deoxyuridine
  参考文献：
  名称：

  A Facile One-Pot Synthesis of 2,3'-Anhydro-2'-Deoxyuridines via 3'-O-Imidazolylsulfonates

  摘要：

  Continued interests in the novel synthetic methods of the pivotal compound, 2,3'-anhydro-2'-deoxyribonucleosides (7) uncovered a facile one-pot conversion of 5 with 1,1'-sulfonyldiimidazole in basic conditions to 7 with almost quantitative yields (91-99%).

  DOI：

  10.1080/00397910008086944

文献信息

• Structure and conformation of 5-methoxymethyl-2′-deoxycytidine
  作者：Zongchao Jia、Guy Tourigny、Louis T. J. Delbaere、Allan L. Stuart、Sagar V. Gupta

  DOI：10.1139/v90-132

  日期：1990.6.1

  The three-dimensional structure of the antiviral agent 5-methoxymethyl-2′-deoxycytidine (MMdCyd) was deduced by X-ray crystallographic analysis. MMdCyd crystallized in space group P2₁ with a = 7.9255(6) Å; b = 16.1505(15) Å, c = 10.1861(5) Å, β = 103.801(5)°, and Z = 4 (2 molecules per asymmetric unit); R = 0.044 (R_w = 0.046) for 2560 observed reflections with net I > 3σ(I). The furanose ring adopts the C(3′)-exo envelope conformation (₃E) in molecule A and the C(2′)-endo envelope conformation (²E) in molecule B. In the sugar ring of both crystallographically independent molecules A and B, the side chain at C(5′) has the g⁺ conformation. This appears to be a preferred geometry required for antiherpes activity in 2′-deoxyribonucleosides. The glycosyl linkage is anti with χ = 213.7° for the A molecule and 222.2° for the B molecule. With respect to this anti conformation, the methoxy group at C(5) in molecules A and B exhibits different conformations; it is on the same side of the pyrimidine plane as the deoxyribofuranose ring oxygen (O4′) in molecule B and on the opposite side in molecule A. Keywords: antiherpes agent, conformation, 5-methoxymethyl-2′-deoxycytidine, crystal structure.

  抗病毒药物5-甲氧甲基-2'-去氧胞苷（MMdCyd）的三维结构通过X射线晶体学分析推导出来。MMdCyd在P2₁空间群中结晶，a = 7.9255(6) Å；b = 16.1505(15) Å，c = 10.1861(5) Å，β = 103.801(5)°，Z = 4（每个非对称单元中有2个分子）；对于2560个观察到的反射，净I > 3σ(I)时，R = 0.044（Rw = 0.046）。呋喃糖环在分子A中采用C(3')-exo信封构象（3E），在分子B中采用C(2')-endo信封构象（2E）。在两个晶体学独立分子A和B的糖环中，C(5')处的侧链呈g+构象。这似乎是2'-去氧腺苷类抗疱疹活性所需的优选几何构型。糖基连接是反式的，A分子的χ为213.7°，B分子为222.2°。相对于这种反式构象，A和B分子中C(5)处的甲氧基呈现不同构象；在B分子中，它与去氧核糖呋喃环氧原子（O4'）位于同一侧，而在A分子中位于相反侧。关键词：抗疱疹药物，构象，5-甲氧甲基-2'-去氧胞苷，晶体结构。
• JIA, ZONGCHAO;TOURIGNY, GUY;DELBAERE, LOUIS T. J.;STUART, ALLAN L.;GUPTA,+, CAN. J. CHEM., 68,(1990) N, C. 836-841
  作者：JIA, ZONGCHAO、TOURIGNY, GUY、DELBAERE, LOUIS T. J.、STUART, ALLAN L.、GUPTA,+

  DOI：——

  日期：——