[5-(Butan-2-yloxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane | 133635-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [5-(Butan-2-yloxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane
• CAS: 133635-48-0
• 化学式: C₁₅H₃₀N₂O₃Si₂
• 分子量: 342.586
• InChiKey: UGVKHQMSMBBGEA-UHFFFAOYSA-N

物化性质

• 沸点：
  358.5±52.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [5-(Butan-2-yloxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 7.0h， 生成 3'-amino-2',3'-dideoxy-5-(1-methylpropoxymethyl)uridine
  参考文献：
  名称：

  3'-氨基-2'，3'-二脱氧尿苷的5-烷氧基甲基衍生物的合成及其抗HIV和癌症活性的评估。

  摘要：

  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。

  DOI：

  10.3891/acta.chem.scand.46-0077
• 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 [5-(Butan-2-yloxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane
  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 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).