1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 135928-55-1

• 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: 1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS: 135928-55-1
• 化学式: C₂₁H₃₀N₂O₅SeSi
• 分子量: 497.525
• InChiKey: ADALFICTXRIPBS-OQIJWPOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三氟化硼乙醚 、 甲基锂 、 silica gel 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Acetic acid (2R,3S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-eth-(E)-ylidene-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Nucleosidic enol esters: A versatile tool for the synthesis of 3′-carbon-substituted nucleosides

  摘要：

  Enol esters of uracil and adenine nucleosides prepared by selenoxide fragmentation of the corresponding 3'-phenylseleno derivatives have been shown to yield 3'-carbon-substituted products upon reacting with MeLi followed by electrophiles, providing the first example of the aldol reaction in this field.

  DOI：

  10.1016/s0040-4039(00)74884-2
• 作为产物：
  描述：

  3'-O-mesyl-2',5'-di-O-pivaloyluridine 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-4-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Nucleosidic enol esters: A versatile tool for the synthesis of 3′-carbon-substituted nucleosides

  摘要：

  Enol esters of uracil and adenine nucleosides prepared by selenoxide fragmentation of the corresponding 3'-phenylseleno derivatives have been shown to yield 3'-carbon-substituted products upon reacting with MeLi followed by electrophiles, providing the first example of the aldol reaction in this field.

  DOI：

  10.1016/s0040-4039(00)74884-2