(S)-(Z)-1-(imidazol-4-yl)pent-1-en-4,5-diol | 935553-94-9

• 英文名称: (S)-(Z)-1-(imidazol-4-yl)pent-1-en-4,5-diol
• 英文别名: (Z,2S)-5-(1H-imidazol-5-yl)pent-4-ene-1,2-diol
• CAS: 935553-94-9
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: GOZBJOSIFUNXSZ-JQSQLHRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(Z)-1-(imidazol-4-yl)pent-1-en-4,5-diol 在 potassium osmate(VI) sodium hydroxide 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 吡啶 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 86.0h， 生成 (5R,7R,8S)-5-tert-butyldiphenylsilyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine-7,8-diol
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomeric imidazolopiperidinoses and imidazoloazepanoses using Wittig/dihydroxylation reactions

  摘要：

  A new route for the synthesis of imidazolosugars-6-deoxyimidazolopiperidinoses 1 and 2 and 7-deoxyimidazoloazepanoses 3 and 4 in two enantiomerical forms-is reported. The new synthetic approach is based on two key reactions: (i) stereocontrolled Wittig Z-olefination of an imidazolecarbaldehyde with phosphoranes containing one chiral centre, obtained from (S)- and (R)-1,2,4-butantriol; (ii) diastereoselective cis-dihydroxylation of previously obtained olefins. All synthesised imidazolosugars were evaluated as potential inhibitors of glycosidases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.016
• 作为产物：
  描述：

  (S)-(Z)-1-[1'-(triphenylmethyl)-1'H-imidazol-4'-yl]-4,5-O-isopropylidene-pent-1-en-4,5-diol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以90%的产率得到(S)-(Z)-1-(imidazol-4-yl)pent-1-en-4,5-diol
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiomeric imidazolopiperidinoses and imidazoloazepanoses using Wittig/dihydroxylation reactions

  摘要：

  A new route for the synthesis of imidazolosugars-6-deoxyimidazolopiperidinoses 1 and 2 and 7-deoxyimidazoloazepanoses 3 and 4 in two enantiomerical forms-is reported. The new synthetic approach is based on two key reactions: (i) stereocontrolled Wittig Z-olefination of an imidazolecarbaldehyde with phosphoranes containing one chiral centre, obtained from (S)- and (R)-1,2,4-butantriol; (ii) diastereoselective cis-dihydroxylation of previously obtained olefins. All synthesised imidazolosugars were evaluated as potential inhibitors of glycosidases. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.016