(R)-methyl 2-(amino)-2-((3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate | 1333312-87-0

• 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: (R)-methyl 2-(amino)-2-((3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate
• 英文别名: methyl (2R)-2-amino-2-[(3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl]acetate
• CAS: 1333312-87-0
• 化学式: C₁₂H₂₅NO₅Si₂
• 分子量: 319.505
• InChiKey: QEFRLXYTSHIUTC-INTQDDNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(amino)-2-((3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate 在 吡啶 作用下， 以 对二甲苯 为溶剂， 反应 9.0h， 以70%的产率得到(3aS,4R,7aS)-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
• 作为产物：
  描述：

  (S)-3-((R)-2-((tert-butyloxycarbonyl)amino)-2-((3S,4S)-4-(2-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetyl)-4-isopropyloxazolidin-2-one 在 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-methyl 2-(amino)-2-((3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate
  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