O,O'-bis(trimethylsilyl)-5-benzyloxymethyluracil | 98808-20-9

• 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: O,O'-bis(trimethylsilyl)-5-benzyloxymethyluracil
• 英文别名: silylated 5-benzyloxymethyl uracil；5-benzyloxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine；5-[(Benzyloxy)methyl]-2,4-bis[(trimethylsilyl)oxy]pyrimidine；trimethyl-[5-(phenylmethoxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxysilane
• CAS: 98808-20-9
• 化学式: C₁₈H₂₈N₂O₃Si₂
• 分子量: 376.603
• InChiKey: AGKDZTUEUUXLMD-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±55.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  O,O'-bis(trimethylsilyl)-5-benzyloxymethyluracil 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 4.0h， 生成 5-(benzyloxy)methyl-2′-deoxyuridine
  参考文献：
  名称：

  Megied, Ahmed E.-S. Abdel; Ali, Omar M.; Kofoed, Thomas, Nucleosides and nucleotides, 2001, vol. 20, # 1-2, p. 1 - 10

  摘要：

  DOI：

文献信息

• Uracil derivatives. V. Syntheses and growth-inhibitory activity against L-1210 cells of 5-substituted 2'-deoxyuridines and orotidine derivatives.
  作者：JUTARO OKADA、KOICHI NAKANO、HIROSHI MIYAKE

  DOI：10.1248/cpb.33.856

  日期：——

  5-Benzyloxymethyl-2'-deoxyuridine 3', 5'-di-p-toluate (III), a key intermediate in the preparation of 5-substituted 2'-deoxyuridines (VIa-d), was prepared in satisfactory yield. 5-(4-Substituted phenylthiomethyl)-2'-deoxyuridines (VIa-d) were synthesized in three steps from III. The reaction of silylated orotates (VIIa-e) with 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-D-ribofuranose (VIII) gave the N1, N3-bisribosides (IXa-e) and the N3-ribosides (Xa-e). The N3-ribosides (Xa-e) were deprotected to give the N3-nucleosides (XIa-e). Compounds VIa-d and XIa-e were tested for ability to inhibit the growth of L-1210 cells in vitro.

  5-苄氧基甲基-2'-脱氧尿苷3', 5'-二对甲苯甲酸酯(III)是制备5-取代的2'-脱氧尿苷(VIa-d)的关键中间体，其收率令人满意。从III开始分三个步骤合成5-(4-取代的苯硫基甲基)-2'-脱氧尿苷(VIa-d)。甲硅烷基化乳清酸酯(VIIa-e)与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖(VIII)反应得到N1,N3-双核糖苷(IXa-e)和N3-核苷（Xa-e）。将N3-核苷(Xa-e)去保护以得到N3-核苷(XIa-e)。测试了化合物VIa-d和XIa-e在体外抑制L-1210细胞生长的能力。
• 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 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).