(4S,5R,6R)-1-Thia-spiro[4.4]non-2-ene-4,6-diol | 849113-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: (4S,5R,6R)-1-Thia-spiro[4.4]non-2-ene-4,6-diol
• 英文别名: (4S,5R,9R)-1-thiaspiro[4.4]non-2-ene-4,9-diol
• CAS: 849113-12-8
• 化学式: C₈H₁₂O₂S
• 分子量: 172.248
• InChiKey: AJWBDAWGNZXJJA-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-1-Thia-spiro[4.4]non-2-ene-4,6-diol 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 5-Fluoro-1-((1R,3R,4R,5R,11R)-7,7,9,9-tetraisopropyl-4-phenylselanyl-6,8,10-trioxa-2-thia-7,9-disila-tricyclo[9.3.0.01,5]tetradec-3-yl)-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
• 作为产物：
  描述：

  (3R,5S,6S)-3-Phenyl-1,4-dioxa-7-thia-dispiro[4.0.4.3]tridec-9-en-2-one 在 三乙烯二胺 、 potassium dioxotetrahydroxoosmate(VI) 六甲基磷酰三胺 、 lithium hydroxide 、 甲基磺酰胺 、 叔丁基锂 、 aluminum isopropoxide 、 potassium carbonate 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 叔丁醇 、 正戊烷 为溶剂， 反应 31.0h， 生成 (4S,5R,6R)-1-Thia-spiro[4.4]non-2-ene-4,6-diol
  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.