(5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane | 857860-08-3

• 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: (5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane
• 英文别名: (5R,6R,7R,8S)-5-azido-6,7,8-tris(phenylmethoxy)-1,4-dioxaspiro[2.5]octane
• CAS: 857860-08-3
• 化学式: C₂₇H₂₇N₃O₅
• 分子量: 473.528
• InChiKey: WCCXJMJBXLZCLM-MZIUKZFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane 在 四丙基高钌酸铵 camphor-10-sulfonic acid 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 15.17h， 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
• 作为产物：
  描述：

  (2R,3R,4S,5S)-2-Azido-6-methylene-tetrahydro-pyran-3,4,5-triol 在 ethylene diamine tetraacetic acid tetrasodium salt Oxone 、 1,1,1-三氟丙酮 、 sodium hydride 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.5h， 生成 (5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane
  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.