嘧啶,5-(甲氧基甲基)-2,4-二[(三甲基甲硅烷基)氧代]- | 133635-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 嘧啶,5-(甲氧基甲基)-2,4-二[(三甲基甲硅烷基)氧代]-
• 英文名称: 5-methoxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine
• 英文别名: [5-(methoxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane
• CAS: 133635-47-9
• 化学式: C₁₂H₂₄N₂O₃Si₂
• 分子量: 300.505
• InChiKey: JTJQTHKPLMGDKO-UHFFFAOYSA-N

物化性质

• 沸点：
  314.1±52.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  53.47
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  嘧啶,5-(甲氧基甲基)-2,4-二[(三甲基甲硅烷基)氧代]- 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-(methoxymethyl)uracil
  参考文献：
  名称：

  2'，3'-didehydro-2'，3'-dideoxynucleosides的新合成。

  摘要：

  3'-碘核苷4和3'-O-甲基磺酰基胸苷9是通过将甲硅烷基化的尿嘧啶2与5-O-叔丁基二苯甲硅烷基-2,3-二脱氧-3-碘-D-苏-戊呋喃糖苷缩合而合成的（3）和甲基5-O-叔丁基二苯基甲硅烷基-2-脱氧-3-甲基磺酰基-D-季戊基呋喃呋喃糖苷（8）。在用甲醇钠处理的消除反应中，核苷4和9产生了相应的2'，3'-二氢-2'，3'-二脱氧核苷5。化合物5b对HIV-1没有抗病毒活性。

  DOI：

  10.3891/acta.chem.scand.45-1060
• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 在 硫酸氢铵 作用下， 反应 8.0h， 生成 嘧啶,5-(甲氧基甲基)-2,4-二[(三甲基甲硅烷基)氧代]-
  参考文献：
  名称：

  Synthesis of various 5-alkoxymethyluracil analogues and structure–cytotoxic activity relationship study

  摘要：

  A number of 5-alkoxymethyluracil analogues were synthesized to evaluate their cytotoxic activity. 5-Alkoxymethyluracil derivatives 1 were prepared via known nucleophilic substitution of 5-chloromethyluracil 5 and subsequently transformed to their corresponding nucleosides 2. All prepared compounds were submitted to cytotoxic activity testing against drug sensitive and drug resistant leukaemia cells and solid tumour derived cell lines. In addition, the cytotoxic activity of 5-alkoxymethyluracil analogues 1 and 2 was compared with the previously published 5-[alkoxy(4-nitrophenyl)methyl]uracil analogues 3 and 4. Extensive structure-cytotoxic activity relationship studies are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.026

文献信息

• Synthesis of 5-Alkoxymethyl Derivatives of 3'-Amino-2',3'-dideoxyuridine and Evaluation of their Activity against HIV and Cancer.
  作者：Mohammed S. Motawia、Ahmed E. S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen、Peter Ebbesen、Daniel R. Carcanague、Ito Chao、K. N. Houk

  DOI：10.3891/acta.chem.scand.46-0077

  日期：——

  3-dideoxy-beta- D-erythro-pentofuranose (3), in the presence of trimethylsilyl triflate as a catalyst, to give the corresponding 3'-phthalimido-2',3'-dideoxynucleosides 5a-f and 6 which on treatment with 33% methylamine-ethanol afforded the corresponding 3'-amino-2',3'-dideoxynucleosides 7a-f and 8 in high yields. Compound 7d showed colony inhibition when tested against human epidermoid cervical cancer cells

  5-烷氧基甲基尿嘧啶2a-c已通过5-羟基甲基尿嘧啶（1）的酸催化醚化反应制备。将化合物1、2a-c，5-甲氧基甲基-和5-苄氧基甲基-尿嘧啶甲硅烷基化并与1,5-二-O-乙酰基-3-邻苯二甲酰亚胺基-2,3-二脱氧-β-D-赤型戊呋喃糖（ 3），在三氟甲磺酸三甲基甲硅烷基酯作为催化剂的存在下，得到相应的3'-邻苯二甲酰亚胺基-2'，3'-二脱氧核苷5a-f和6，将其用33％甲胺-乙醇处理后得到相应的3'-氨基-2'，3'-二脱氧核苷7a-f和8的产量很高。当针对人表皮样宫颈癌细胞进行测试时，化合物7d显示出集落抑制作用。核苷5a-e，7a-f和8没有显示出对HIV-1的任何显着活性。
• Synthesis and Anti-HIV Activity of 5-Alkoxymethyl-3′-azido-2′,3′-dideoxyuridines
  作者：Ahmed E.-S. Abdel-Megied、Poul Hansen、Erik B. Pedersen、Claus Nielsen、Carsten M. Nielsen

  DOI：10.1002/ardp.19933260702

  日期：——

  Methyl 3‐azido‐5‐O‐tert‐butyldiphenylsilyl‐2,3‐dideoxy‐D‐erythro‐furanoside (3) was coupled with silylated 5‐hydroxymethyluracil (1a) and its C1‐C6 alkyl ethers 1b–g to give the corresponding protected nucleosides 4a‐g which were deprotected with Bu4NF to afford 3‐azido nucleosides 5a‐g and 6a‐g. The α‐anomers 6f,g show moderate activity against HIV. No significant activity against HSV‐1 was found

  甲基3-叠氮基-5-O-叔丁基二苯基甲硅烷基-2,3-双脱氧-D-赤型-呋喃糖苷(3)与甲硅烷基化的5-羟甲基尿嘧啶(1a)及其C1-C6烷基醚1b-g偶联得到相应的受保护核苷 4a-g 用 Bu4NF 脱保护，得到 3-叠氮核苷 5a-g 和 6a-g。α-端基异构体 6f、g 对 HIV 表现出中等活性。未发现化合物 5 和 6 对 HSV-1 具有显着活性。
• Synthesis of 2?,3?-dideoxynucleosides from 5-alkoxymethyluracils
  作者：Ahmed E. -S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1007/bf00815166

  日期：——

  A modified synthesis of protected 2,3-dideoxyribose 5 starting from L-glutamic acid (1) is described. Reaction of 5 with silylated 5-hydroxymethyluracil 7 a and 5-alkoxymethyluracils 7 b-e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2',3'-dideoxyuridine derivatives 8 a-e and 9 a-e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides 10 a-e and 11 a-e. Treatment of 9 b-e with tri(1H-1,2,4-triazol-1-yl) phosphine oxide and subsequent reaction of 12 b-e with ammonia in dioxane afforded the cytosine derivatives 13 b-e which on treatment with methanolic ammonia gave the corresponding 2',3'-dideoxycytidine derivatives 14 b-e and 15 b-e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).