3-deoxy-6-O-(4-bromophenyl)-1,2-O-isopropylidene-D-glucofuranoside | 1067651-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-deoxy-6-O-(4-bromophenyl)-1,2-O-isopropylidene-D-glucofuranoside
• 英文别名: (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-bromophenoxy)ethanol
• CAS: 1067651-69-7
• 化学式: C₁₅H₁₉BrO₅
• 分子量: 359.217
• InChiKey: WMLXQEDYWVXOMN-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-6-O-(4-bromophenyl)-1,2-O-isopropylidene-D-glucofuranoside 在 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到5-azido-3,5-dideoxy-6-O-(4-bromophenyl)-1,2-O-isopropylidene-L-lyxo-hexofuranose
  参考文献：
  名称：

  Design and Synthesis of Potent and Selective BACE-1 Inhibitors

  摘要：

  Highly potent BACE-1 protease inhibitors have been developed from ill inhibitors containing a hydroxyethylene (HE) core displaying aryloxymethyl or benzyloxymethyl P1 side chain and a methoxy P1' side chain. The target molecules were synthesized in good overall yields from chiral carbohydrate starting materials. The inhibitors show high BACF-1 potency and good selectivity against cathepsin D, where the most potent inhibitor Furnishes BACE-1 Ki << 1 nM and displays > 1000-fold selectivity over cathepsin D.

  DOI：

  10.1021/jm901168f
• 作为产物：
  描述：

  4-溴苯酚 、 (3aR,5S,6aR)-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到3-deoxy-6-O-(4-bromophenyl)-1,2-O-isopropylidene-D-glucofuranoside
  参考文献：
  名称：

  WO2008/119773

  摘要：

  公开号：

文献信息

• WO2008/119773
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and Synthesis of Potent and Selective BACE-1 Inhibitors
  作者：Catarina Björklund、Stefan Oscarson、Kurt Benkestock、Neera Borkakoti、Katarina Jansson、Jimmy Lindberg、Lotta Vrang、Anders Hallberg、Åsa Rosenquist、Bertil Samuelsson

  DOI：10.1021/jm901168f

  日期：2010.2.25

  Highly potent BACE-1 protease inhibitors have been developed from ill inhibitors containing a hydroxyethylene (HE) core displaying aryloxymethyl or benzyloxymethyl P1 side chain and a methoxy P1' side chain. The target molecules were synthesized in good overall yields from chiral carbohydrate starting materials. The inhibitors show high BACF-1 potency and good selectivity against cathepsin D, where the most potent inhibitor Furnishes BACE-1 Ki << 1 nM and displays > 1000-fold selectivity over cathepsin D.