(3aR,4R,7aR)-methyl octahydro-1,1,3,3-tetramethyl-6-oxo-[1,2,5]oxadisilolo[3,4-c]pyridine-4-carboxylate | 1333312-83-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,4R,7aR)-methyl octahydro-1,1,3,3-tetramethyl-6-oxo-[1,2,5]oxadisilolo[3,4-c]pyridine-4-carboxylate
• CAS: 1333312-83-6
• 化学式: C₁₁H₂₁NO₄Si₂
• 分子量: 287.463
• InChiKey: NQDSUZSAZWEUIF-JEZHCXPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7aR)-methyl octahydro-1,1,3,3-tetramethyl-6-oxo-[1,2,5]oxadisilolo[3,4-c]pyridine-4-carboxylate 在 lithium aluminium tetrahydride 、 二氟化氢钾 、 双氧水 作用下， 以 乙醚 、 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以68%的产率得到Fagomine; 桑叶生物碱; (2R,3R,4R)-2-羟甲基哌啶-3,4-二醇
  参考文献：
  名称：

  Silicon-mediated asymmetric synthesis of fagomine and 3,4-di-epi-fagomine

  摘要：

  The synthesis of D-fagomine and its stereoisomer, D-3,4-di-epi-fagomine has been achieved from C(2)-symmetric 3,4-bis-silyl substituted adipic acid di-oxazolidin-2-one derivatives via stereocontrolled azidation and silicon to hydroxyl conversion as the key steps. The Evans oxazolidin-2-one controlled the stereochemical outcome of the azidation which supersedes the directing effects of the silyl substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.004
• 作为产物：
  描述：

  (R)-methyl 2-((tert-butyloxycarbonyl)amino)-2-((3R,4R)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以99%的产率得到(3aR,4R,7aR)-methyl octahydro-1,1,3,3-tetramethyl-6-oxo-[1,2,5]oxadisilolo[3,4-c]pyridine-4-carboxylate
  参考文献：
  名称：

  Silicon-mediated asymmetric synthesis of fagomine and 3,4-di-epi-fagomine

  摘要：

  The synthesis of D-fagomine and its stereoisomer, D-3,4-di-epi-fagomine has been achieved from C(2)-symmetric 3,4-bis-silyl substituted adipic acid di-oxazolidin-2-one derivatives via stereocontrolled azidation and silicon to hydroxyl conversion as the key steps. The Evans oxazolidin-2-one controlled the stereochemical outcome of the azidation which supersedes the directing effects of the silyl substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.004