ethyl (3S)-3-[(2S,3S,4R,5R,6R)-6-azido-2-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-3-hydroxypropanoate | 857860-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (3S)-3-[(2S,3S,4R,5R,6R)-6-azido-2-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-3-hydroxypropanoate
• CAS: 857860-14-1
• 化学式: C₃₂H₃₇N₃O₈
• 分子量: 591.661
• InChiKey: NZPBRLCYLYOVBT-SRTFTMACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-3-[(2S,3S,4R,5R,6R)-6-azido-2-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-3-hydroxypropanoate 在 palladium dihydroxide 甲酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 48.0h， 以62%的产率得到(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one
  参考文献：
  名称：

  Novel Synthesis of Castanospermine and 1-Epicastanospermine

  摘要：

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

  DOI：

  10.1021/ol0508577
• 作为产物：
  描述：

  在 四丙基高钌酸铵 正丁基锂 、 N-甲基吗啉氧化物 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 ethyl (3S)-3-[(2S,3S,4R,5R,6R)-6-azido-2-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-3-hydroxypropanoate
  参考文献：
  名称：

  Novel Synthesis of Castanospermine and 1-Epicastanospermine

  摘要：

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

  DOI：

  10.1021/ol0508577

文献信息

• Novel Synthesis of Castanospermine and 1-Epicastanospermine
  作者：Linda Cronin、Paul V. Murphy

  DOI：10.1021/ol0508577

  日期：2005.6.1

  Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates lid the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.