5'-O-(thexyldimethylsilyl)anhydrothymidine | 123533-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-O-(thexyldimethylsilyl)anhydrothymidine
• 英文别名: (1R,9R,10R)-10-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-4-methyl-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one
• CAS: 123533-05-1
• 化学式: C₁₈H₃₀N₂O₄Si
• 分子量: 366.533
• InChiKey: QMYJBPPSBXXMDI-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-O-(thexyldimethylsilyl)anhydrothymidine 在 palladium on activated charcoal sodium azide 、 Dowex 50(H+) 、 氢气 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  3'-取代-2'，3'-二脱氧核苷类似物的合成作为潜在的抗抑郁药

  摘要：

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。

  DOI：

  10.1016/s0040-4039(00)99623-0
• 作为产物：
  描述：

  [(2R,3S,5R)-2-[[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 以98%的产率得到5'-O-(thexyldimethylsilyl)anhydrothymidine
  参考文献：
  名称：

  3'-取代-2'，3'-二脱氧核苷类似物的合成作为潜在的抗抑郁药

  摘要：

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。

  DOI：

  10.1016/s0040-4039(00)99623-0

文献信息

• N- versus O-Alkylation of 2,3'-anhydrothymidine: reaction of the obtained pyrimidinium salts with azide ion
  作者：Catherine Goulaouic、David R. Adams、Angele Chiaroni、Claude Riche、David S. Grierson

  DOI：10.1021/jo00063a021

  日期：1993.5

  Reaction of 5'-O-(thexyldimethylsilyl)anhydrothymidine (1) with O-(mesitylenesulfonyl)hydroxylamine and CH3OTf generates the pyrimidinium salts 3a and 3b which react with azide ion to give the N3-substituted AZT derivatives 4a and 4b, respectively. In contrast, alkylation of 1 with pentyl triflate occurs at both the N3 and 04 positions leading, after treatment with NaN3, to the expected AZT analog 4d and the novel 3-substituted 2,3-dideoxyxylofuranosyl azide 7d. In a further study, the extent to which competing 04-alkylation occurs was found to be sensitive to steric factors, increasing in the order MeOTf < EtOTf < pentyl OTf < i-PrOTf. Formation of the alternate 04-alkylated AZT derivatives 9 via an intramolecular Hilbert-Johnson process was not observed in these reactions. It was demonstrated, however, that reaction of the intermediate O4-alkylated pyridinium salt 6c with Me4NCl does evolve toward the corresponding C-3' chloro compound 14c. Reaction of 1 with the less reactive alkylating agent (EtO)2P(O)CH2OTf is more complicated producing the O-alkylated product 7f and the novel dimer 19.
• Preparation and Anti-HIV Activity of N-3-Substituted Thymidine Nucleoside Analogs
  作者：David R. Adams、Caroline Perez、Michel Maillard、Jean-Claude Florent、Michel Evers、Yvette Hénin、Simon Litvak、Laura Litvak、Claude Monneret、David S. Grierson

  DOI：10.1021/jm9600095

  日期：1997.5.1

  A series of 22 derivatives of AZT substituted at the N-3 position of the thymine base were prepared and evaluated for anti-HIV activity in cell culture (Lai strain of HIV-1 in CEM-c113 cells). The AZT analogs bearing a N-3 amino group (7), a hydroxyalkyl chain (12f), and a phosphonomethyl (12k) substituent displayed activities in the 0.045-0.082 mu M range. The analogs 12d, 12e, 12q, 15, and 19 were active at <0.5 mu M concentration. Compound 18 in which two molecules of AZT are connected at N-3 via a two-carbon link and ''dimer'' II also displayed significant; activity. To obtain information concerning the mechanism of RT inhibition by these AZT analogs, compounds 7, 12d, 12e, and 12q were incubated with recombinant HIV-1 RT in the presence of poly(A)-oligo[dT((12-18))] and poly(C)-oligo[dG((12-18))] template-primers. In contrast to AZT-TP (control), none of these nucleosides displayed any significant inhibition of RT in the recombinant enzyme assay, indicating that phosphorylation is a necessary prerequiste for activity.
• MAILLARD, MICHEL;FARAJ, ABDESSLEM;FRAPPIER, FRANCOIS;FLORENT, JEAN-CLAUDE+, TETRAHEDRON LETT., 30,(1989) N5, C. 1955-1958
  作者：MAILLARD, MICHEL、FARAJ, ABDESSLEM、FRAPPIER, FRANCOIS、FLORENT, JEAN-CLAUDE+

  DOI：——

  日期：——