1,4-anhydro-2-deoxy-2-(thymin-1-yl)-L-arabinitol | 174955-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,4-anhydro-2-deoxy-2-(thymin-1-yl)-L-arabinitol
• 英文别名: [3R-(3α,4β,5α)]-5-Methyl-1-[tetrahydro-4-hydroxy-5-(hydroxymethyl)-3-furanyl]2,4(1H,3H)pyrimidinedione；1-[(3S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 174955-59-0
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: PVDLLCLDSAFEFJ-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-2-(thymin-1-yl)-L-arabinitol 在 吡啶 作用下， 反应 72.0h， 生成 Acetic acid (2S,3R,4S)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of Isonucleoside 5′-Triphosphates

  摘要：

  A series of isonucleoside 5'-triphosphates were synthesized via a rapid and efficient method. The structures of the triphosphates (8a-8d) were characterized by (PNMR)-P-31 and TOF-MS.

  DOI：

  10.1081/scc-120020202
• 作为产物：
  描述：

  胸腺嘧啶 在 sodium tetrahydroborate 、 18-冠醚-6 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 81.67h， 生成 1,4-anhydro-2-deoxy-2-(thymin-1-yl)-L-arabinitol
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x

文献信息

• Solid-phase synthesis and evaluation of TAR RNA targeted β-carboline–nucleoside conjugates
  作者：Peng Zhao、Hong-Wei Jin、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1039/b809598a

  日期：——

  Four types of β-carboline–nucleoside conjugates were synthesized. The binding affinities of these β-carboline–nucleoside conjugates 4–11, 13 and 15 to TAR RNA were evaluated by affinity capillary electrophoresis. The data of binding affinities to TAR RNA show that conjugates 9 and 13 are stronger binders than the parent compound MC3. Computer modeling indicates that the β-carboline–nucleoside conjugate 13 can fit to the UCU three-nucleotide bulge region of TAR RNA.

  我们合成了四种δ-咔啉核苷共轭物。亲和毛细管电泳分析了这些δ-咔啉核苷共轭物 4â11、13 和 15 与 TAR RNA 的结合亲和力。与 TAR RNA 的结合亲和力数据显示，轭合物 9 和 13 的结合力强于母体化合物 MC3。计算机建模表明，δ-咔啉核苷共轭物 13 能与 TAR RNA 的 UCU 三核苷酸隆起区吻合。
• Stereoselective synthesis of l-isonucleosides
  作者：Sı́lvia Aragonès、Fernando Bravo、Yolanda Dı́az、Ma̱ Isabel Matheu、Sergio Castillón

  DOI：10.1016/s0040-4039(03)00743-3

  日期：2003.5

  L-Isonucleosides 17 and 19 were stereoselectively synthesised from (S)-glycidol by two different procedures. The key step was the synthesis of a chiral dihydrofuran which was carried out by oxidation/elimination of 8 and by ring-closing metathesis of diene 10. The procedure can be applied to the synthesis of both enantiomers. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and Duplex Stabilization of Oligonucleotides Consisting of Isonucleosides
  作者：Zhenjun Yang、Huyi Zhang、Jimei Min、Lingtai Ma、Lihe Zhang

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2037::aid-hlca2037>3.0.co;2-i

  日期：1999.11.10

  Novel oligonucleotide analogues built from isonucleosides were synthesized by the phosphoramidite approach on an automated DNA synthesizer. The phosphoramidite building blocks were synthesized by phosphitylation of the corresponding protected isonucleosides. The oligonucleotide analogues C - G containing the isonucleoside 1-3 were studied with respect to their hybridization properties and enzymatic stability. The oligomers bearing an isonucleoside at the end of the strands all proved stable towards snake-venom phosphodiesterase, but only the oligomers D-G exhibit acceptable duplex stability when hybridized with complementary d(A(14)).