(R)-((2R,3S,3aS,6aR)-3-(allyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate | 1262487-76-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-((2R,3S,3aS,6aR)-3-(allyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate
• CAS: 1262487-76-2
• 化学式: C₂₅H₂₄O₆
• 分子量: 420.462
• InChiKey: JNWDUCQVSGYOKE-OEDNBQTASA-N

反应信息

• 作为反应物：
  描述：

  (R)-((2R,3S,3aS,6aR)-3-(allyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate 在 palladium 10% on activated carbon 、 水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以81%的产率得到(R)-((2S,3S,3aR,6aR)-3-hydroxy-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate
  参考文献：
  名称：

  Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

  摘要：

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.016
• 作为产物：
  描述：

  (R)-((2R,3R,4R)-3-(allyloxy)-4,5-dihydroxy-tetrahydrofuran-2-yl)(phenyl)methyl cinnamate 在 丙二酸环(亚)异丙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到(R)-((2R,3S,3aS,6aR)-3-(allyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate
  参考文献：
  名称：

  Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

  摘要：

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.016