(R)-methyl 2-((tert-butyloxycarbonyl)amino)-2-((3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl)acetate | 1333312-86-9

• 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-((tert-butyloxycarbonyl)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-[(3S,4S)-4-(2-methoxy-2-oxoethyl)-2,2,5,5-tetramethyl-1,2,5-oxadisilolan-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 1333312-86-9
• 化学式: C₁₇H₃₃NO₇Si₂
• 分子量: 419.623
• InChiKey: SFOQJEFBQOWPJN-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-((tert-butyloxycarbonyl)amino)-2-((3S,4S)-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， 以96%的产率得到(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
• 作为产物：
  描述：

  (4S,4'S)-3,3'-(2,2'-((3S,4S)-2,2,5,5-tetramethyl-1,2,5-oxadisilolane-3,4-diyl)bis(acetyl))bis(4-isopropyloxazolidin-2-one) 在 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 25.63h， 生成 (R)-methyl 2-((tert-butyloxycarbonyl)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