(5S)-5-tert-butyldiphenylsilyloxymethyl-5,6-dihydroimidazo[1,5-a]pyridine | 935553-99-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5S)-5-tert-butyldiphenylsilyloxymethyl-5,6-dihydroimidazo[1,5-a]pyridine
• CAS: 935553-99-4
• 化学式: C₂₄H₂₈N₂OSi
• 分子量: 388.585
• InChiKey: JVGMRKHTCPXZHC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.05
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S)-5-tert-butyldiphenylsilyloxymethyl-5,6-dihydroimidazo[1,5-a]pyridine 在 potassium osmate(VI) 甲基磺酰胺 、 四丁基氟化铵 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 62.0h， 生成 (5S,7R,8S)-5,6,7,8-tetrahydro-5-hydroxymethylimidazo[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：

  (R)-(Z)-1-[1'-(triphenylmethyl)-1'H-imidazol-4'-yl]-4,5-O-isopropylidene-pent-1-en-4,5-diol 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 丙酮 为溶剂， 反应 42.0h， 生成 (5S)-5-tert-butyldiphenylsilyloxymethyl-5,6-dihydroimidazo[1,5-a]pyridine
  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