4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidin-2-one | 87418-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidin-2-one
• CAS: 87418-74-4
• 化学式: C₂₉H₂₉N₃O₆
• 分子量: 515.566
• InChiKey: DSCRHXNXUNMGQD-ZRIRBKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidin-2-one 在 吡啶 、 N-甲基咪唑 、 2,4,6-三甲基苯磺酰氯 、 一水合肼 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 7.83h， 生成
  参考文献：
  名称：

  An Improved Synthesis of 1-β-D-Arabinofuranosylcytosine 5′-Phosphate-L-1,2-diacylglycerols

  摘要：

  5'-O-MMTr-cytosine arabinoside was prepared on a large scale from 5'-0-MMTr-cytidine with diphenyl carbonate via 5'-protected cytidine - 2',3'-carbonate -- aracytidine-2',2-anhydro derivative at a 67 % yield. The synthesis of 1,2-L-dipalmitoyl-sn-glycerol, 1,2-L-distearoyl-sn-glycerol and 1,2-L-dioleoyl-sn-glycerol described here using 9-fluorenylmethoxycarbonyl (FMOC) group for protection of 3-position of glycerol which can be selectively removed by Et3N treatment on the overall 60-70 % yield based on 1,2,-isopropilidene-sn-glycerol. These glycerols were phosphorylated first with 2-chlorophenyl-phosphoro-bis-triazolide quantitatively(1) in order to avoid acyl migration, then the glycerophosphate intermediates were condensed with 2',3',N-4-trileulinyl-1-beta-D-arabinofuranosylcytosine in the presence of 2-mesytilenesulphonyl chloride (MsCl) and 1-methylimidazole (MeIm)- which was used in the coupling of nucleotides(2)- in an 85-95 % yield compared with the low yielding diester method of Ryu(3.) Deblocking was carried out in two steps with tetrabutylammonium fluoride (TBAF) and hydrazine hydrate, producing target compouns (14a, 14b, 14c) at a 50 % yield.

  DOI：

  10.1080/07328319808004734
• 作为产物：
  描述：

  胞苷 在 吡啶 、 碳酸二苯酯 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of 1-β-d-arabinofuranosyl-cytosine 5′-phosphate-l-1,2-diacylglycerols

  摘要：

  5'-O-MMTr-cytosine arabinoside was prepared on a large scale from 5'-O-MMTr-cytidine with diphenyl carbonate via 5'-protected cytidine-2',3'-carbonate-ara-cytidine-2',2-anhydro derivative at a 67% yield. 1,2-Dipalmitoyl-sn-glycerol, 1,2-distearoyl-sn-glycerol and 1,2-dioleoyl-sn-glycerol were phosphorylated first with 2-chlorphenyl-phosphorobis-triazolide quantitatively (Welch and Chattopadhyaya, 1985. Acta Chem. Scand. B39, 47-57). This method was used in order to avoid acyl migration, then the glycerophosphate intermediates were condensed with 2',3',N-4-trileulinyl-1-beta-D-arabinofuranosylcytosine in the presence of 2-mesytilensulphonyl chloride (MSCI) and 1-methylimidazole (MeIm)-which was used in the coupling of nucleotides (Nyilas et al., 1986. Acta Chem. Scand. B40, 678-684)-in an 85-88% yield compared with the low yielding diester method of Ryu et al., 1982. J. Med. Chem. 25, 1322-1329. Deblocking was carried out in two steps with tetrabutylammonium fluoride (TBAF) and hydrazine hydrate, producing target compounds (9a, 9b, 9c) at a 50% yield. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00056-x

文献信息

• Hybridization properties of oligoarabinonucleotides
  作者：Paul Apostolos Giannaris、Masad José Damha

  DOI：10.1139/v94-118

  日期：1994.3.1

  of stereochemistry at the C2′ of ribonucleotides does not have a negative effect on interaction with natural sequences. In fact, in complexes with poly dT, oligoarabinoadenylates displayed greater hybridization affinity than oligoriboadenylates. In summary, we observed that (i) ara(Ap)7A interacted favourably with poly rU and poly dT, (ii) ara(Cp)7C formed a stable complex with poly rG; (iii) ara(Up)7U

  制备了阿糖胞苷、阿糖腺苷和阿糖尿苷的 3'-亚磷酰胺衍生物，并将其用于寡阿糖核苷酸（阿拉伯糖核酸或 ANA）的固相合成。热变性分析和凝胶迁移率变化分析用于研究 ANA 与互补 DNA 和 RNA 之间的相互作用。一般来说，ANA/DNA 和 ANA/RNA 复合物的解链温度与相应的 DNA/DNA 和 DNA/RNA 复合物的解链温度相当。因此，核糖核苷酸 C2' 的立体化学倒置对与天然序列的相互作用没有负面影响。事实上，在与聚 dT 的复合物中，低聚阿拉伯糖腺苷酸比低聚阿拉伯糖腺苷酸显示出更大的杂交亲和力。总之，我们观察到 (i) ara(Ap)7A 与 poly rU 和 poly dT 有良好的相互作用，(ii) ara(Cp)7C与poly rG形成稳定的复合物；(iii) ara(Up)7U 不与互补的 poly rA 结合；(iv) 混合寡聚阿拉伯糖核苷酸ara(UCU UCC
• Ogilvie, Kelvin K.; McGee, Danny P. C.; Boisvert, Suzanne M., Canadian Journal of Chemistry, 1983, vol. 61, p. 1204 - 1212
  作者：Ogilvie, Kelvin K.、McGee, Danny P. C.、Boisvert, Suzanne M.、Hakimelahi, Gholam H.、Proba, Zbigniew A.

  DOI：——

  日期：——