benzyl (4R,5R)-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate | 1148110-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (4R,5R)-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1148110-91-1
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: XASBFSJWHLMEAT-SPUZQDLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4R,5R)-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 反应 14.42h， 以97%的产率得到
  参考文献：
  名称：

  The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation

  摘要：

  The first enantioselective synthesis of protected imino-digitoxose (-)-16 was attained Starting with a synthetic intermediate of polyoxin C prepared by the L-threonine aldolase-catalyzed aldol condensation of (2S,3S)-2,3-O-isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of an intramolecular nucleophilic attack by a Cbz-protected amino group on the hemiacetal Carbon, a side reaction in the synthesis of natural products, for the formation of the piperidine ring of the imino-sugar. Imino-deoxydigitoxose (+)-18 was also synthesized from (-)-16 by reduction and acid hydrolysis. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.12.029
• 作为产物：
  描述：

  benzyl (4R,5R)-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-[(4-methylphenyl)sulfonyloxymethyl]-1,3-oxazolidine-3-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 18.0h， 以67%的产率得到benzyl (4R,5R)-5-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation

  摘要：

  The first enantioselective synthesis of protected imino-digitoxose (-)-16 was attained Starting with a synthetic intermediate of polyoxin C prepared by the L-threonine aldolase-catalyzed aldol condensation of (2S,3S)-2,3-O-isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of an intramolecular nucleophilic attack by a Cbz-protected amino group on the hemiacetal Carbon, a side reaction in the synthesis of natural products, for the formation of the piperidine ring of the imino-sugar. Imino-deoxydigitoxose (+)-18 was also synthesized from (-)-16 by reduction and acid hydrolysis. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.12.029