N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-β-D-ribofuranosyl)cytosine | 1006032-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-β-D-ribofuranosyl)cytosine
• 英文别名: N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-β-D-ribofuranosyl)cytosine；N-[1-[(3aR,4R,6R,6aS)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 1006032-34-3
• 化学式: C₃₅H₃₉N₃O₅SeSi
• 分子量: 688.757
• InChiKey: QJFXHJMUQSSSQP-SSKIFPDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-β-D-ribofuranosyl)cytosine 在 三氟乙酸 作用下， 反应 1.0h， 以100%的产率得到1-(4-seleno-β-D-ribofuranosyl)-N⁴-benzoylcytosine
  参考文献：
  名称：

  Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides

  摘要：

  Stereoselective synthesis of novel 2',3'-didehydro-2',3'dideoxy-4'-selenonnucleosides (4'-seleno-d4Ns) 4a-c was accomplished via 4'-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4'-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic gamma-lactone using a Pummerer-type condensation as a key step. Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine.

  DOI：

  10.1021/jo8003277
• 作为产物：
  描述：

  [(3aS,4R,6aR)-2,2-dimethyl-5-oxo-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxol-4-yl]methoxy-tert-butyl-diphenylsilane 、 N4-苯甲酰基胞嘧啶 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 1.0h， 以35%的产率得到N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-4-seleno-β-D-ribofuranosyl)cytosine
  参考文献：
  名称：

  First Synthesis of 4‘-Selenonucleosides Showing Unusual Southern Conformation

  摘要：

  The first synthesis of 4'-selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4'-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2'-endol C3'-exo twist (Southern) conformation.

  DOI：

  10.1021/ol7025558