methyl 5-azido-3,5-dideoxy-6-O-phenyl-L-lyxo-hexofuranoside | 1067651-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 5-azido-3,5-dideoxy-6-O-phenyl-L-lyxo-hexofuranoside
• 英文别名: (3R,5S)-5-[(1S)-1-azido-2-phenoxyethyl]-2-methoxyoxolan-3-ol
• CAS: 1067651-85-7
• 化学式: C₁₃H₁₇N₃O₄
• 分子量: 279.296
• InChiKey: ZZVSHBUGHXCPKH-FXJUQPSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-azido-3,5-dideoxy-6-O-phenyl-L-lyxo-hexofuranoside 、 碘甲烷 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到methyl 5-azido-3,5-dideoxy-6-O-phenyl-2-O-methyl-L-lyxo-hexofuranoside
  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：

  甲醇 、 5-azido-3,5-dideoxy-6-O-phenyl-1,2-O-isopropylidene-L-lyxo-hexofuranose 在 盐酸 作用下， 反应 2.0h， 以98%的产率得到methyl 5-azido-3,5-dideoxy-6-O-phenyl-L-lyxo-hexofuranoside
  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

文献信息

• 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.