5'-O-(4,4'-dimethoxytrityl)-N⁴-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine | 109420-85-1

• 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: 5'-O-(4,4'-dimethoxytrityl)-N⁴-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine
• 英文别名: 5'-O-(dimethoxytrityl)-4-N-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine；5'-O-DMT-N⁴-Fmoc-cytidine；N4-Fmoc-5'-O-DMT-deoxycytidine；9H-fluoren-9-ylmethyl N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 109420-85-1
• 化学式: C₄₅H₄₁N₃O₈
• 分子量: 751.836
• InChiKey: UHZALBNSLACKAR-MQFHWOLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-N⁴-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine 、 N-(9-fluorenylmethoxycarbonyl)-L-alanyl fluoride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到5'-O-(4,4'-dimethoxytrityl)-4-N-(9-fluorenylmethoxycarbonyl)-2'-deoxy-3'-O-[N-(9-fluorenylmethoxycarbonyl)-L-alanyl]cytidine
  参考文献：
  名称：

  Aminoacylation of Nucleosides with FMOC Amino Acid Fluorides¹

  摘要：

  DOI：

  10.1021/jo9601674
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 生成 5'-O-(4,4'-dimethoxytrityl)-N⁴-(9-fluorenylmethoxycarbonyl)-2'-deoxycytidine
  参考文献：
  名称：

  The 9-Fluorenylmethoxycarbonyl (Fmoc) Group and Its Use in Oligonucleotide Synthesis

  摘要：

  The introduction of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group into the exocyclic amino function of 2'-deoxynucleosides and their dimethoxytritylation and phosphitylation is described. The resulting key intermediates were investigated in the built-up of different oligodeoxyribonucleoside phosphate and thiophosphate chains which were deprotected under mild basic conditions leading to crude oligomers of high purity.

  DOI：

  10.1080/07328319908044667

文献信息

• Synthesis and Biochemical Evaluation of Phosphonoformate Oligodeoxyribonucleotides
  作者：Christina M. Yamada、Douglas J. Dellinger、Marvin H. Caruthers

  DOI：10.1021/ja060112b

  日期：2006.4.1

  acid linker. Synthons were sequentially added to this support using tetrazole as an activator, oxidized to phosphonoformate, and the transient 5'-protecting group was removed with acid. Following total synthesis of an oligomer, protecting groups were removed with TEMED.HF and products purified by HPLC. These analogues were resistant to nucleases, formed duplexes with complementary RNA (A-form), and,

  膦甲酸寡脱氧核糖核苷酸是通过固相合成策略制备的。制备合适的合成子的第一步是在金属钠存在下将双（N，N-二异丙基氨基）膦和氯甲酸二苯基甲基甲硅烷基乙酯缩合，得到甲酸，[双（N，N-二异丙基氨基）膦基]-β-（二苯基甲基甲硅烷基乙基）酯。然后使用4,5-二氰基咪唑将该反应的产物与适当保护的2'-脱氧核苷缩合以产生3'-O-亚膦酰胺反应性单体。胞嘧啶、腺嘌呤和鸟嘌呤的环外胺用 9-芴基甲氧羰基保护，并使用氢醌-O，O'-二乙酸接头在受控孔玻璃上合成寡脱氧核糖核苷酸。使用四唑作为活化剂，将合成子依次添加到该载体中，氧化成膦甲酸酯，并用酸去除瞬时 5'-保护基团。在低聚物全合成后，用TEMED.HF去除保护基团并通过HPLC纯化产物。这些类似物对核酸酶具有抗性，与互补 RNA（A 型）形成双链体，并且作为在选定位点含有磷酸盐的嵌合寡聚体，刺激了 RNase H1 活性。
• Gaur; Bobde; Atreyi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 2, p. 108 - 112
  作者：Gaur、Bobde、Atreyi、Gupta

  DOI：——

  日期：——
• Solid phase synthesis of a model nucleopeptide with a phosphodiester bond between the 5′ end of a trinucleotide and a serine residue
  作者：Jordi Robles、Enrique Pedroso、Anna Grandas

  DOI：10.1016/s0040-4039(00)92178-6

  日期：1991.1

  The model nucleopeptide Boc-Ser(pTCT)-NHcHex has been assembled on a polystyrene solid support using the phosphite triester approach. Fmoc and cyanoethyl groups have been used to protect the exocyclic amine of cytosine and phosphate groups respectively. Final deprotection has been carried out by treatment with methanolic potassium carbonate.
• Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N,N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group
  作者：Yuanzhong Zhou、Stanislav Chladek、Louis J. Romano

  DOI：10.1021/jo00082a011

  日期：1994.2

  A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-C-8-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-C-8-AAF gave N-[N-2-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (N2-Fmoc-dG- and N-[O-6-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O-6-Fmoc-dG-C-8-AAF). The 5'-OH of N-2-FmoodG-C-8-AAF was protected using 4,4'-dimethoxrytrityl chloride to yield 5/-Dh4T-N-2-Fmoc-dG-C-8-AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similarly. The stability of Fmoc-protected C-8-AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite in solid-phase DNA synthesis.
• GAUR, R. K.;BOBDE, V.;ATREYI, M.;GUPTA, K. C., INDIAN J. CHEM. B, 29,(1990) N, C. 108-112
  作者：GAUR, R. K.、BOBDE, V.、ATREYI, M.、GUPTA, K. C.

  DOI：——

  日期：——