3-Benzoyl-1-[(3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl]-5-fluoro-1H-pyrimidine-2,4-dione | 206762-88-1

• 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: 3-Benzoyl-1-[(3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl]-5-fluoro-1H-pyrimidine-2,4-dione
• 英文别名: 3-benzoyl-1-[(3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 206762-88-1
• 化学式: C₃₉H₃₉FN₂O₅SSi
• 分子量: 694.899
• InChiKey: KWCIGMHAJACXLT-VATRIRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Benzoyl-1-[(3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl]-5-fluoro-1H-pyrimidine-2,4-dione 在 氟化铵 、 ammonium hydroxide 、 氢氟酸 、 三氯化硼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-Fluoro-1-((3S,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-3-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Novel Iso-4‘-thionucleosides Using the Mitsunobu Reaction

  摘要：

  A novel class of isomeric 4'-thionucleosides with the base moiety at the 2'-position was synthesized from D-glucose. The coupling of 1,4-anhydro-4-thioarabitol (13) with various nucleobases using the Mitsunobu reaction was investigated. With both purines and N-3-benzoyluracils, the reaction predominantly gave beta-isomers, suggesting that these were produced via an episulfonium intermediate. The beta-anomers produced by the reaction of N-3-benzoyluracils included both N- and O-alkylated derivatives. Interestingly, only the reaction of N-3-benzoyluracil gave a mixture of N-alkylated adduct (20d) and O-alkylated bipyrimidinyl adduct (22), the structure of which was unambiguously determined by NMR spectroscopic data including HMBC and NOE. Deprotection of the Mitsunobu reaction products gave the desired iso-4'-thionucleosides.

  DOI：

  10.1021/jo980667s
• 作为产物：
  描述：

  (3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-ol 、 N3-BZ-5-氟尿嘧啶 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 以18%的产率得到3-Benzoyl-1-[(3S,4S,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl]-5-fluoro-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Novel Iso-4‘-thionucleosides Using the Mitsunobu Reaction

  摘要：

  A novel class of isomeric 4'-thionucleosides with the base moiety at the 2'-position was synthesized from D-glucose. The coupling of 1,4-anhydro-4-thioarabitol (13) with various nucleobases using the Mitsunobu reaction was investigated. With both purines and N-3-benzoyluracils, the reaction predominantly gave beta-isomers, suggesting that these were produced via an episulfonium intermediate. The beta-anomers produced by the reaction of N-3-benzoyluracils included both N- and O-alkylated derivatives. Interestingly, only the reaction of N-3-benzoyluracil gave a mixture of N-alkylated adduct (20d) and O-alkylated bipyrimidinyl adduct (22), the structure of which was unambiguously determined by NMR spectroscopic data including HMBC and NOE. Deprotection of the Mitsunobu reaction products gave the desired iso-4'-thionucleosides.

  DOI：

  10.1021/jo980667s

文献信息

• Synthesis of Novel Iso-4‘-thionucleosides Using the Mitsunobu Reaction
  作者：Kohei Yamada、Shinji Sakata、Yuichi Yoshimura

  DOI：10.1021/jo980667s

  日期：1998.10.1

  A novel class of isomeric 4'-thionucleosides with the base moiety at the 2'-position was synthesized from D-glucose. The coupling of 1,4-anhydro-4-thioarabitol (13) with various nucleobases using the Mitsunobu reaction was investigated. With both purines and N-3-benzoyluracils, the reaction predominantly gave beta-isomers, suggesting that these were produced via an episulfonium intermediate. The beta-anomers produced by the reaction of N-3-benzoyluracils included both N- and O-alkylated derivatives. Interestingly, only the reaction of N-3-benzoyluracil gave a mixture of N-alkylated adduct (20d) and O-alkylated bipyrimidinyl adduct (22), the structure of which was unambiguously determined by NMR spectroscopic data including HMBC and NOE. Deprotection of the Mitsunobu reaction products gave the desired iso-4'-thionucleosides.