1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine | 136317-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine
• 英文别名: 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl]thymine
• CAS: 136317-58-3
• 化学式: C₂₂H₄₀N₂O₇Si₂
• 分子量: 500.74
• InChiKey: FXSUFWJWZYCZNU-HDAAZOAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  112.01
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 1-{5-O-(4-monomethoxytrityl)-2-O-[2-(4-nitrophenyl)ethoxycarbonyl]-3-O-succinoyl-α-D-arabinofuranosyl}thymine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113
• 作为产物：
  描述：

  1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)thymine 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.75h， 生成 1-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides

  摘要：

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.

  DOI：

  10.1080/15257770500267113

文献信息

• Synthesis and hybridization studies of α-configured arabino nucleic acids
  作者：Pankaj Gupta、Jyotirmoy Maity、Gaurav Shakya、Ashok K. Prasad、Virinder S. Parmar、Jesper Wengel

  DOI：10.1039/b905019c

  日期：——

  Synthesis of α-L-arabino- and α-D-arabino-configured pentofuranosyl nucleosides of four of the natural bases [thymine (ara-T), adenine (ara-A), cytosine (ara-C) and guanine (ara-G)] is reported together with hybridization properties of oligonucleotides containing α-L-ara-T and -A, α-D-ara-T and -A, and 2′-amino-α-L-ara-T monomers. 2′-O-Acetylated α-L-ara-T, -A, -C and -G, α-D-ara-T, -A, -C and -G,

  四个天然碱的α-L-阿拉伯糖和α-D-阿拉伯糖构型的呋喃呋喃糖基核苷的合成[胸腺嘧啶 （一只老鼠）， 腺嘌呤 （ara-A）， 胞嘧啶 （ara-C） 和 鸟嘌呤（ara-G）]与含有α-L-ara-T和-A，α-D-ara-T和-A以及2'-氨基-α-L-ara-T的寡核苷酸的杂交特性一起报道。单体。2' - O-乙酰化的α-L-ara-T，-A，-C和-G，α-D-ara-T，-A，-C和-G和N2'-酰化的α-L-合成了ara-T亚磷酰胺结构单元，并将其与标准DNA亚磷酰胺一起用于18-mer寡核苷酸的固相合成。热变性实验表明，掺入了三到六种阿拉伯糖-配置成DNA-寡核苷酸的单体降低了对反平行DNA / RNA补体的结合亲和力。完全修饰的α-L-ara-寡核苷酸不与DNA / RNA互补序列杂交，而证实了完全修饰的α-D-ara-寡核苷酸与互补DNA / RNA在平行链方向上的杂交。