N-[6-Oxo-7-((1R,3R,5S,11S)-7,7,9,9-tetraisopropyl-6,8,10-trioxa-2-thia-7,9-disila-tricyclo[9.3.0.0^1,5]tetradec-3-yl)-6,7-dihydro-1H-purin-2-yl]-acetamide | 849113-08-2

• 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: N-[6-Oxo-7-((1R,3R,5S,11S)-7,7,9,9-tetraisopropyl-6,8,10-trioxa-2-thia-7,9-disila-tricyclo[9.3.0.0^1,5]tetradec-3-yl)-6,7-dihydro-1H-purin-2-yl]-acetamide
• CAS: 849113-08-2
• 化学式: C₂₇H₄₅N₅O₅SSi₂
• 分子量: 607.922
• InChiKey: PSDMWSOMJKXFRP-HCUOBIAZSA-N

反应信息

• 作为反应物：
  描述：

  N-[6-Oxo-7-((1R,3R,5S,11S)-7,7,9,9-tetraisopropyl-6,8,10-trioxa-2-thia-7,9-disila-tricyclo[9.3.0.0^1,5]tetradec-3-yl)-6,7-dihydro-1H-purin-2-yl]-acetamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-[7-((2R,4S,5R,6S)-4,6-Dihydroxy-1-thia-spiro[4.4]non-2-yl)-6-oxo-6,7-dihydro-1H-purin-2-yl]-acetamide
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained 2‘-Deoxy-4‘-thia β-Anomeric Spirocyclic Nucleosides Featuring Either Hydroxyl Configuration at C5‘

  摘要：

  An enantioselective approach to 2'-deoxy-4'-thia spirocyclic nucleosides featuring an alpha- or beta-hydroxyl substituent at C-5' of the carbocyclic ring is detailed. The starting point is the mandelate acetal 8. The overall strategy involves the stereocontrolled dihydroxylation of this dihydrothiophene, subsequent generation of the keto acetonide 12 followed by its Meerwein-Ponndorf-Verley reduction and beta-elimination, protection of the resulting dihydroxy thiaglycal, electrophilic glycosidation according to the Haraguchi protocol, reductive removal of the phenylseleno group, and end-game global deprotection. Acquisition of the alpha- and beta-5'-isomers is equally facile. Various ID and 2D NMR techniques are used for assigning configuration.

  DOI：

  10.1021/jo048071u
• 作为产物：
  描述：

  在 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以100%的产率得到N-[6-Oxo-7-((1R,3R,5S,11S)-7,7,9,9-tetraisopropyl-6,8,10-trioxa-2-thia-7,9-disila-tricyclo[9.3.0.0^1,5]tetradec-3-yl)-6,7-dihydro-1H-purin-2-yl]-acetamide
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained 2‘-Deoxy-4‘-thia β-Anomeric Spirocyclic Nucleosides Featuring Either Hydroxyl Configuration at C5‘

  摘要：

  An enantioselective approach to 2'-deoxy-4'-thia spirocyclic nucleosides featuring an alpha- or beta-hydroxyl substituent at C-5' of the carbocyclic ring is detailed. The starting point is the mandelate acetal 8. The overall strategy involves the stereocontrolled dihydroxylation of this dihydrothiophene, subsequent generation of the keto acetonide 12 followed by its Meerwein-Ponndorf-Verley reduction and beta-elimination, protection of the resulting dihydroxy thiaglycal, electrophilic glycosidation according to the Haraguchi protocol, reductive removal of the phenylseleno group, and end-game global deprotection. Acquisition of the alpha- and beta-5'-isomers is equally facile. Various ID and 2D NMR techniques are used for assigning configuration.

  DOI：

  10.1021/jo048071u