(+)-(1S,2R,3R,7R,7aR)-1,2,7-triacetoxy-3-(acetoxymethyl)hexahydro-1H-pyrrolizine | 620160-83-0

• 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: (+)-(1S,2R,3R,7R,7aR)-1,2,7-triacetoxy-3-(acetoxymethyl)hexahydro-1H-pyrrolizine
• 英文别名: [(1S,2R,3R,7R,8R)-1,2,7-triacetyloxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-3-yl]methyl acetate
• CAS: 620160-83-0
• 化学式: C₁₆H₂₃NO₈
• 分子量: 357.361
• InChiKey: MHBFJGSNXYALFS-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R,3R,7R,7aR)-1,2,7-triacetoxy-3-(acetoxymethyl)hexahydro-1H-pyrrolizine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以92%的产率得到(+)-(1S,2R,3R,7R,7aR)-hexahydro-3-hydroxymethyl-1H-pyrrolizine-1,2,7-triol
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-7-Epiaustraline and (+)-1,7-Diepiaustraline

  摘要：

  A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.

  DOI：

  10.1021/jo034914q
• 作为产物：
  描述：

  (-)-(1S,2R,3R,7R,7aR)-1,2,7-triacetoxy-3-(phenylmethoxy)methylhexahydro-1H-pyrrolizine 在 palladium dichloride 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 (+)-(1S,2R,3R,7R,7aR)-1,2,7-triacetoxy-3-(acetoxymethyl)hexahydro-1H-pyrrolizine
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-7-Epiaustraline and (+)-1,7-Diepiaustraline

  摘要：

  A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.

  DOI：

  10.1021/jo034914q