O^5'-(4-methoxy-trityl)-cytidine | 64481-90-9

• 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: O^5'-(4-methoxy-trityl)-cytidine
• 英文别名: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidin-2-one
• CAS: 64481-90-9
• 化学式: C₂₉H₂₉N₃O₆
• 分子量: 515.566
• InChiKey: DSCRHXNXUNMGQD-MIRJVGOZSA-N

物化性质

• 沸点：
  716.1±70.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

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：

  O^5'-(4-methoxy-trityl)-cytidine 在 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
• 作为产物：
  描述：

  胞苷 在 吡啶 、 4-二甲氨基吡啶 、 硫酸氢铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 73.0h， 生成 O^5'-(4-methoxy-trityl)-cytidine
  参考文献：
  名称：

  核苷。LI部分2-（4-硝基苯基）乙氧羰基（npeoc）和2-（2,4-二硝基苯基）乙氧羰基（dnpeoc）用于保护核糖核苷和2'-脱氧核糖核苷中的羟基官能团†

  摘要：

  常见的2'-脱氧嘧啶和-嘌呤核苷，胸腺嘧啶核苷（4），O 4- [2-（4-硝基苯基）乙基]-胸苷（17），2'-脱氧-N 4- [2-（4-硝基苯基） ）乙氧基羰基]胞嘧啶核苷（26），2'-脱氧-N 6- [2-（4-硝基苯基）-乙氧基羰基]腺苷-39和2'-脱氧-N 2- [2-（4-硝基苯基）（乙氧基羰基） ] -O 6- [2-4硝基苯基）乙基]-鸟苷（52）在糖部分的OH功能上进一步受到2-（4-硝基苯基）乙氧羰基（npeoc）和2-（2,4-二硝基苯基）乙氧羰基（dnpeoc）基团的保护，形成了新的部分和完全封闭的中间体核苷和核苷酸合成。相应的5'-O-单甲氧衍生物5，18，30，40，和56也被用来作为起始原料来合成，其没有被直接酰化得到一些其他的中间体。在核糖核苷系列中，5' - ö -monomethoxytrityl衍生物14，36，49，和63与2-（4-硝基苯基）

  DOI：

  10.1002/hlca.19930760122

文献信息

• Regiodefined synthesis and conformational properties of adenyldiyl trimers with unsymmetrical 2′–5′ and 3′–5′ internucleotide linkages
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Ryoji Noyori

  DOI：10.1016/0040-4020(95)00590-5

  日期：——

  Adenyldiyl trimers with different kinds of substitucnts on 2′–5′ and 3′–5′ phosphate linkages have been synthesized in a general, regiodefined manner. Examination of the 2D NMR spectra reveals that the trimers with adenylyl(2′–5′)adenosine linkage make a syn-anti as well as syn-syn base slack between the two adenyl bases and exist as a mixture of the two conformers.

  以一般的区域定义方式合成了在2'-5'和3'-5'磷酸键上具有不同取代基的Adenyldiyl三聚体。2D NMR谱图的检查表明，带有腺苷基（2'–5'）腺苷键的三聚体在两个腺苷酸碱基之间形成顺-反和顺-syn-顺碱基松弛，并且以两个构象异构体的混合物形式存在。
• An Improved Synthesis of 1-β-D-Arabinofuranosylcytosine 5′-Phosphate-L-1,2-diacylglycerols
  作者：Ágnes Nyilas

  DOI：10.1080/07328319808004734

  日期：1998.9

  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.
• Okupniak, Janina; Adamiak, Ryszard W.; Wiewiorkowski, Maciej, Polish Journal of Chemistry, 1981, vol. 55, # 3, p. 679 - 682
  作者：Okupniak, Janina、Adamiak, Ryszard W.、Wiewiorkowski, Maciej

  DOI：——

  日期：——
• SCHIRMEISTER, H.;PFLEIDERER, W., NUCLEOSIDES AND NUCLEOTIDES, 6,(1987) N 1-2, 501-503
  作者：SCHIRMEISTER, H.、PFLEIDERER, W.

  DOI：——

  日期：——
• Synthesis of 1-β-d-arabinofuranosyl-cytosine 5′-phosphate-l-1,2-diacylglycerols
  作者：Ágnes Nyilas

  DOI：10.1016/s0009-3084(97)00056-x

  日期：1997.9

  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.