(2R,3S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-chloro-purin-9-yl)-tetrahydro-thiophen-3-ol | 214280-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2R,3S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-chloro-purin-9-yl)-tetrahydro-thiophen-3-ol
• 英文别名: (2R,3S,4S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(6-chloropurin-9-yl)thiolan-3-ol
• CAS: 214280-00-9
• 化学式: C₂₆H₂₉ClN₄O₂SSi
• 分子量: 525.146
• InChiKey: YHJBLGFUNFQSLQ-XPNTWCBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  98.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-chloro-purin-9-yl)-tetrahydro-thiophen-3-ol 在 氟化铵 、 氢氟酸 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 (2R,3S,4S)-4-(6-Chloro-purin-9-yl)-2-hydroxymethyl-tetrahydro-thiophen-3-ol
  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 在 三氯化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (2R,3S,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(6-chloro-purin-9-yl)-tetrahydro-thiophen-3-ol
  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.