(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 | 1333312-85-8

• 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: (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
• 英文别名: tert-butyl N-[(1R)-2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]-1-[(3S,4S)-2,2,5,5-tetramethyl-4-[2-oxo-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethyl]-1,2,5-oxadisilolan-3-yl]ethyl]carbamate
• CAS: 1333312-85-8
• 化学式: C₂₇H₄₇N₃O₉Si₂
• 分子量: 613.856
• InChiKey: MUXBJDLEVMTPQS-PIBZIWMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 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 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.63h， 生成 (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
  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