tert-butyl N4-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate | 1182206-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N4-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate
• 英文别名: tert-butyl N6-(benzyloxycarbonyl)-8-(hydroxymethyl)adenine-9-acetate
• CAS: 1182206-90-1
• 化学式: C₂₀H₂₃N₅O₅
• 分子量: 413.433
• InChiKey: SLMHXGLXAUQBJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  128.46
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N4-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 {S-[N6-(benzyloxycarbonyl)-9-(ω-carbonylmethyl)adenine-8-methyl]-N-Fmoc-L-cysteine methyl ester}-S-{N6-(benzyloxycarbonyl)-9-[(tert-butoxy)carbonylmethyl]adenine-8-methyl}-L-cysteine
  参考文献：
  名称：

  Autonomously Pairing Cysteinyl-Linked Nucleotide Analogues with a Unique Architecture

  摘要：

  We report the efficient pairing in water of the first representative of oligonucleotide analogues in which the backbone is replaced by linking elements between the nucleobases. The architecture of the new analogue demonstrates that the structural differentiation of oligonucleotides into a contiguous backbone and nucleobases, as embodied by the natural nucleic acids and all nucleotide analogues analyzed to date, is not a prerequisite for pairing. UV and circular dichroisrn analyses of self-complementary and non-self-complementary octanucleotide analogues strongly suggest the fully reversible, sequence-specific association of our new analogues to form a left-handed double helix with an antiparallel strand orientation that is characterized by melting temperatures and free enthalpies higher than those of natural RNA and DNA of the same sequence. The linking element incorporates an L-cysteine moiety that allows a short and efficient synthesis of the monomeric building blocks and, through the choice of either L- or D-cysteine, gives access to either one of the enantiomeric oligomers and thus to left- or right-handed helices.

  DOI：

  10.1021/ja200829s
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 6-N-(benzyloxycarbonyl)-9-(tert-butoxycarbonylmethyl)adenine 在 正丁基锂 、 二异丙胺 、 溶剂黄146 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 正己烷 、 乙醇 为溶剂， 以78%的产率得到tert-butyl N4-[(benzyloxy)carbonyl]-8-(hydroxymethyl)adenine-9-acetate
  参考文献：
  名称：

  具有整合的碱基和骨干的寡核苷酸类似物。第20部分†

  摘要：

  Abstractmagnified imageHydrazide‐ and amide‐linked oligonucleoside analogues with integrated bases and backbone were designed to allow for a rapid synthesis of long and water‐soluble oligomers. The uracil‐, cytosine‐, and adenine‐derived hydrazide building blocks 13–15 were synthesized by nucleophilic substitution with the hydrazine 23 of the halides 19, 28, and 34, derived from the alcohols 18, 27, and 33, respectively, while the uracil‐, cytosine‐, and adenine‐derived amide building blocks 45–47 were synthesized by a Curtius degradation of the carboxylic acids 51, 56, and 61. These acids were obtained by Wittig reaction of the aldehydes 49, 53, and 58. The guanine‐derived monomers 44 and 48 were synthesized by reductive cyclisation of the nitroso amides 38 and 63, respectively, resulting from acylation of the known 2,6‐diamino‐4‐(benzyloxy)‐5‐nitrosopyrimidine (37).

  DOI：

  10.1002/hlca.200900047