(1S,2S,3S,6S,7S,7aS)-2,6,7-triacetoxy-1-(acetoxymethyl)-3-methyl-pyrrolizidine | 1122458-46-1

• 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: (1S,2S,3S,6S,7S,7aS)-2,6,7-triacetoxy-1-(acetoxymethyl)-3-methyl-pyrrolizidine
• CAS: 1122458-46-1
• 化学式: C₁₇H₂₅NO₈
• 分子量: 371.387
• InChiKey: BVRZQYITAMYVPF-XRJMIXERSA-N

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,6S,7S,7aS)-2,6,7-triacetoxy-1-(acetoxymethyl)-3-methyl-pyrrolizidine 在 氨 作用下， 以 甲醇 为溶剂， 以97%的产率得到(1S,2S,3S,6S,7S,7aS)-2,6,7-trihydroxy-1-(hydroxymethyl)-3-methyl-pyrrolizidine
  参考文献：
  名称：

  Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated γ-lactone

  摘要：

  The 1,3-dipolar cycloaddition of the cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to the single adduct 7 which can be transformed into the 3-epi-1-homo-casuarine via a reaction sequence involving reduction of the lactone moiety and N-O bond hydrogenolysis, followed by intramolecular alkylation of the nitrogen atom. The adduct 7 can also be used in the synthesis of 1-methyl- or 3-methyl analogues of 3-epi-casuarine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.016
• 作为产物：
  描述：

  (1S,2S,3S,6S,7S,7aS)-2,6,7-trihydroxy-1-(hydroxymethyl)-3-methyl-pyrrolizidine 、 乙酸酐 在 三乙胺 作用下， 生成 (1S,2S,3S,6S,7S,7aS)-2,6,7-triacetoxy-1-(acetoxymethyl)-3-methyl-pyrrolizidine
  参考文献：
  名称：

  Synthesis of casuarine-related derivatives via 1,3-dipolar cycloaddition between a cyclic nitrone and an unsaturated γ-lactone

  摘要：

  The 1,3-dipolar cycloaddition of the cyclic nitrone derived from tartaric acid and (S)-5-hydroxymethyl-2(5H)-furanone leads to the single adduct 7 which can be transformed into the 3-epi-1-homo-casuarine via a reaction sequence involving reduction of the lactone moiety and N-O bond hydrogenolysis, followed by intramolecular alkylation of the nitrogen atom. The adduct 7 can also be used in the synthesis of 1-methyl- or 3-methyl analogues of 3-epi-casuarine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.016