(3aR,8R,8aR)-2-benzyl-8-t-butyldiphenylsiloxymethyl-6,6-dimethyl-5,7-dioxa-isoxazolidino[4,5]cycloheptane | 929008-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,8R,8aR)-2-benzyl-8-t-butyldiphenylsiloxymethyl-6,6-dimethyl-5,7-dioxa-isoxazolidino[4,5]cycloheptane
• CAS: 929008-34-4
• 化学式: C₃₂H₄₁NO₄Si
• 分子量: 531.767
• InChiKey: JNOPKZIRQMXGKV-NSGJQZOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,8R,8aR)-2-benzyl-8-t-butyldiphenylsiloxymethyl-6,6-dimethyl-5,7-dioxa-isoxazolidino[4,5]cycloheptane 在 palladium on activated charcoal 吡啶 、 四丁基氟化铵 、 氨 、 氢气 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.17h， 生成 (-)-N-acetyl-isofagomine
  参考文献：
  名称：

  Synthesis of (−)‐Isofagomine

  摘要：

  1,3-Dipolar cycloaddition of N-benzyl nitrone 2 to delta-lactone 15 proceeded with excellent stereoselectivity to provide only one adduct 16. Cycloadduct 16 was subsequently subjected to a sequence of reactions involving rearrangement to gamma-lactone, glycolic cleavage/reduction, protection of the terminal hydroxymethyl group, reduction of the lactone, desilylation/mesylation, and hydrogenolysis of the N-O bond providing (-)-isofagomine and its N-substituted derivatives. The biologic activity of N-substituted (-)-isofagomines toward commercially available alpha- and beta-glucosidases, alpha-D-mannosidase, alpha-L-fucosidase, beta-D-glucuronidase, and beta-D-galactosidase was tested.

  DOI：

  10.1080/07328300601039336
• 作为产物：
  描述：

  (3aR,6R,6aS,1'R)-2-benzyl-6-(1',2'-dihydroxyethyl)-4-oxo-isoxazolidino[4,5-c]tetrahydrofuran 在 4-二甲氨基吡啶 、 sodium periodate 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (3aR,8R,8aR)-2-benzyl-8-t-butyldiphenylsiloxymethyl-6,6-dimethyl-5,7-dioxa-isoxazolidino[4,5]cycloheptane
  参考文献：
  名称：

  Synthesis of (−)‐Isofagomine

  摘要：

  1,3-Dipolar cycloaddition of N-benzyl nitrone 2 to delta-lactone 15 proceeded with excellent stereoselectivity to provide only one adduct 16. Cycloadduct 16 was subsequently subjected to a sequence of reactions involving rearrangement to gamma-lactone, glycolic cleavage/reduction, protection of the terminal hydroxymethyl group, reduction of the lactone, desilylation/mesylation, and hydrogenolysis of the N-O bond providing (-)-isofagomine and its N-substituted derivatives. The biologic activity of N-substituted (-)-isofagomines toward commercially available alpha- and beta-glucosidases, alpha-D-mannosidase, alpha-L-fucosidase, beta-D-glucuronidase, and beta-D-galactosidase was tested.

  DOI：

  10.1080/07328300601039336