2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one | 667411-76-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one
• 英文别名: N-[5-[(2R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,5-dihydrofuran-2-yl]-6-oxo-1H-pyrimidin-2-yl]benzamide
• CAS: 667411-76-9
• 化学式: C₂₈H₄₃N₃O₅Si₂
• 分子量: 557.838
• InChiKey: YOKHGVVJWGSCSG-FYYLOGMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  98.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one 在 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 氟化氢吡啶 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 37.17h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  A Short, Efficient Synthesis of 2′-Deoxypseudoisocytidine Based on Heck-Chemistry

  摘要：

  A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.

  DOI：

  10.1081/ncn-120025239
• 作为产物：
  描述：

  1,4-脱水-2-脱氧-3,5-二-O-[二甲基(2-甲基-2-丙基)硅烷基]-D-赤式-戊-1-烯糖 、 2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine 在 N,O-双三甲硅基乙酰胺 、 palladium diacetate 、 三苯胂 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 以68%的产率得到2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one
  参考文献：
  名称：

  A Short, Efficient Synthesis of 2′-Deoxypseudoisocytidine Based on Heck-Chemistry

  摘要：

  A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.

  DOI：

  10.1081/ncn-120025239

文献信息

• A Short, Efficient Synthesis of 2′-Deoxypseudoisocytidine Based on Heck-Chemistry
  作者：Alain Mayer、Christian J. Leumann

  DOI：10.1081/ncn-120025239

  日期：2003.10.1

  A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.