1-((2R,3R,3aR,6aR,9aS)-5,5-Di-tert-butyl-3-phenylselanyl-hexahydro-4,6-dioxa-1-thia-5-sila-cyclopenta[d]inden-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((2R,3R,3aR,6aR,9aS)-5,5-Di-tert-butyl-3-phenylselanyl-hexahydro-4,6-dioxa-1-thia-5-sila-cyclopenta[d]inden-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(1S,3R,4R,5R,9R)-7,7-ditert-butyl-4-phenylselanyl-6,8-dioxa-2-thia-7-silatricyclo[7.3.0.01,5]dodecan-3-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₇H₃₈N₂O₄SSeSi
• 分子量: 593.721
• InChiKey: BKHGTWDBAAMBTD-XXXNKJRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二叔丁基氯硅烷 在 2,4,6-三甲基吡啶 、 N,O-双三甲硅基乙酰胺 、 silver trifluoromethanesulfonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 1-((2R,3R,3aR,6aR,9aS)-5,5-Di-tert-butyl-3-phenylselanyl-hexahydro-4,6-dioxa-1-thia-5-sila-cyclopenta[d]inden-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  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

文献信息

• Stereoselective Synthesis of Conformationally Constrained 2‘-Deoxy-4‘-thia β-Anomeric Spirocyclic Nucleosides Featuring Either Hydroxyl Configuration at C5‘
  作者：Shuzhi Dong、Leo A. Paquette

  DOI：10.1021/jo048071u

  日期：2005.3.1

  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.