[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-methyl-amine | 158226-51-8

• 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: [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-methyl-amine
• CAS: 158226-51-8
• 化学式: C₂₈H₄₀N₂O₄Si
• 分子量: 496.722
• InChiKey: OAVCCRONKHJEJM-QWDLEPIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.31
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-methyl-amine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到(3aS,4R,5R,6R,6aS)-4-Benzyloxy-6-benzyloxymethyl-2-methylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol
  参考文献：
  名称：

  Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

  摘要：

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.

  DOI：

  10.1016/s0040-4039(00)73136-4
• 作为产物：
  描述：

  (1S,2S,3R,4R,5S)-2-Amino-3-benzyloxy-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol 在 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-methyl-amine
  参考文献：
  名称：

  Synthesis of demethylallosamidin, a yeast chitinase inhibitor; use of disaccharide glycosyl donor carrying novel neighboring group

  摘要：

  In the synthesis of novel pseudotrisaccharide called demethylallosamidin, a thioglycoside carrying the 2-acetamido group served as an efficient glycosyl donor through undergoing specific N,O-isopropylidenation at the 2- and 3-positions which prohibits oxazoline ring formation during the glycosidation reaction.

  DOI：

  10.1016/s0040-4039(00)73136-4