(1S,2S,3S,6S,7S,7aS)-6,7-di-tert-butoxy-2-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)-1-(pivaloyloxymethyl)-pyrrolizidine | 1122458-07-4

• 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)-6,7-di-tert-butoxy-2-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)-1-(pivaloyloxymethyl)-pyrrolizidine
• CAS: 1122458-07-4
• 化学式: C₅₄H₇₇NO₆Si₂
• 分子量: 892.379
• InChiKey: KOBRAONADJURDL-PVUFLCEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  63.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,6S,7S,7aS)-6,7-di-tert-butoxy-2-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)-1-(pivaloyloxymethyl)-pyrrolizidine 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 以90%的产率得到(1S,2S,3S,6S,7S,7aS)-6,7-di-tert-butoxy-2-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)-1-hydroxymethyl-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)-6,7-di-tert-butoxy-3-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-1-(pivaloyloxymethyl)-pyrrolizidine 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(1S,2S,3S,6S,7S,7aS)-6,7-di-tert-butoxy-2-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)-1-(pivaloyloxymethyl)-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