4-N-acetyl-2',5'-bis-O-(tert-butyldimethylsilyl)cytidine | 121055-61-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-acetyl-2',5'-bis-O-(tert-butyldimethylsilyl)cytidine
• 英文别名: 2',5'-Bis(O-tert-butyldimethylsilyl)-N⁴-acetylcytidine；N-[1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 121055-61-6
• 化学式: C₂₃H₄₃N₃O₆Si₂
• 分子量: 513.782
• InChiKey: QVNUASALOYYGRL-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-N-acetyl-2',5'-bis-O-(tert-butyldimethylsilyl)cytidine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 72.0h， 生成 N⁴-acetyl-2',5'-di-O-tert-butyldimethylsilyl-3'-deoxycytidine
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 N-乙酰胞嘧啶核苷 在 吡啶 作用下， 反应 48.0h， 以65%的产率得到4-N-acetyl-2',5'-bis-O-(tert-butyldimethylsilyl)cytidine
  参考文献：
  名称：

  3'-C-氰基-3'-脱氧核苷的合成及其抗病毒活性。

  摘要：

  已经合成了一系列的3'-C-氰基-3'-脱氧核苷，并将其评估为抗病毒剂。2'，5'-双-O-（叔丁基二甲基甲硅烷基）-β-D-赤型五氟呋喃糖-尿嘧啶3'-核糖基衍生物，4-N-乙酰胞嘧啶和腺嘌呤与氰化钠的反应生成差向异构体混合物氰醇，在3'-脱氧后产生相应的3'-C-氰基-3'-脱氧-β-D-木基戊呋喃糖基衍生物10。这些化合物被差向异构为相应的β-D-核糖-戊呋喃糖基衍生物11。 10和11的甲硅烷基化得到脱保护的3'-C-氰基-3'-脱氧-β-D-二甲苯基和-核戊五呋喃糖基核苷。尿苷，胞苷和腺嘌呤的这些衍生物，以及3'-C-氰基-2'，3'的3'-C-氰基-3'-脱氧β-D-二甲苯基和-ribo-pentofuranosyl。评估了胸腺嘧啶的-二脱氧-β-D-苏-和-赤-五呋喃糖基和3'-C-氰基-2'，3'-二脱氧-β-D-甘油-戊-2'-异呋喃糖基衍生物。它们的抗病毒活性。在对宿主

  DOI：

  10.1021/jm00128a011

文献信息

• Synthesis of 5'-Deoxy-5'-Difluoromethyl Phosphonate Nucleotide Analogs
  作者：Jasenka Matulic-Adamic、Peter Haeberli、Nassim Usman

  DOI：10.1021/jo00113a040

  日期：1995.4

  synthetic route to nucleoside 5'-deoxy-5'-difluoromethyl phosphonates from ribofuranosyl 5-deoxy-5-difluoromethyl phosphonate precursors is described. Methyl 5,6-dideoxy-6-(diethoxyphosphinyl)-6.6-difluoro-2,3-O-isopropylidene-beta-D-ribo-hexofuranoside (7) was converted, under mild conditions, to the suitable glycosylating agent 1-O-acetyl-2,3-di-O-benzoyl-5,6-dideoxy-6,6-difluoro-beta-D-ribo-hexofuranoside (10). 1,2-Di-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-P-D-ribo-hexofuranoside (16) was also prepared as a versatile building block for nucleotide synthesis. Condensation of 10 with silylated nucleobases, followed by complete deprotection, afforded 5',6'-dideoxy-6'-(dihydroxyphosphinyl)-6'6'-difluoro nucleoside analogs 22a-c. In the case of the glycosylation of adenine, a considerable quantity of N-7 regioisomer 19 was formed. 5',6'-Dideoxy-6'-(dihydroxyphosphinyl)-6 adenosine analog 22e was converted into the triphosphate analog 23 using 1,1'-carbonyldiimidazole activation followed by condensation with pyrophosphate. The adenosine 3',5-cyclic monophosphate analog 24 was obtained through the DCC promoted intramolecular cyclization of 22c. Dinucleoside phosphate analog 27 was prepared by DCC-catalyzed coupling of 1-[2,3-di-O-benzoyl-5,6-dideoxy-6-(dihydroxyphosphinyl)-6,6-difluoro-P-D-ribo-hexofuranosyl]uracil (21a) with 2',5'-bis(O-tert-butyldimethylsilyl)-N-4-cytidine (25), followed by deprotection.
• CAMARASA, MARIA-JOSE;DIAZ-ORTIZ, ANGEL;CALVO-MATEO, ANNA;HERAS, FEDERICO +, J. MED. CHEM., 32,(1989) N, C. 1732-1738
  作者：CAMARASA, MARIA-JOSE、DIAZ-ORTIZ, ANGEL、CALVO-MATEO, ANNA、HERAS, FEDERICO +

  DOI：——

  日期：——