(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde | 857860-12-9

• 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: (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde
• 英文别名: (2R,3S,4R,5R,6R)-6-azido-2-methoxy-3,4,5-tris(phenylmethoxy)oxane-2-carbaldehyde
• CAS: 857860-12-9
• 化学式: C₂₈H₂₉N₃O₆
• 分子量: 503.555
• InChiKey: JTRXODZSXDBCOU-DFLSAPQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde 在 palladium dihydroxide 正丁基锂 、 甲酸 、 氢气 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、3.45 MPa 条件下， 反应 48.5h， 生成 (1R,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：

  2,3,4-tri-O-benzyl-6-deoxy-D-xylo-hex-5-enopyranosyl azide 在 四丙基高钌酸铵 、 ethylene diamine tetraacetic acid tetrasodium salt Oxone 、 1,1,1-三氟丙酮 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.67h， 生成 (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde
  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.