methyl (2S,3R)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate | 945264-62-0

• 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: methyl (2S,3R)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 945264-62-0
• 化学式: C₁₉H₂₅NO₇
• 分子量: 379.41
• InChiKey: WTMWNBNPQAKJAL-JONQDZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate 在 甲醇 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到benzyl N-[(1R,2R)-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dihydroxypropan-2-yl]carbamate
  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：

  、 碘甲烷 在 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以106.7 mg的产率得到methyl (2S,3R)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Nishiyama, Toshihiro; Mohile, Swapnil Surendra; Kajimoto, Tetsuya, Heterocycles, 2007, vol. 71, # 6, p. 1397-1405+3

  摘要：

  DOI：

文献信息

• Nishiyama, Toshihiro; Mohile, Swapnil Surendra; Kajimoto, Tetsuya, Heterocycles, 2007, vol. 71, # 6, p. 1397-1405+3
  作者：Nishiyama, Toshihiro、Mohile, Swapnil Surendra、Kajimoto, Tetsuya、Node, Manabu

  DOI：——

  日期：——
• The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation
  作者：Toshihiro Nishiyama、Tetsuya Kajimoto、Swapnil S. Mohile、Noboru Hayama、Teppei Otsuda、Minoru Ozeki、Manabu Node

  DOI：10.1016/j.tetasy.2008.12.029

  日期：2009.2

  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.