(2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate | 1262487-66-0

• 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: (2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate
• 英文别名: [(2R,3S,3aS,6aR)-5-oxo-2-[(R)-phenyl(phenylmethoxy)methyl]-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 1262487-66-0
• 化学式: C₂₉H₂₆O₆
• 分子量: 470.522
• InChiKey: ZYHXFFDWMGJCQJ-NWDIXFLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(+)-crassalactone B
  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：

  (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one 、 cinnamoyl 2,4,6-trichlorobenzoyl mixed anhydride 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以0.07 g的产率得到(2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl 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

文献信息

• Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone
  作者：Gangavaram V.M. Sharma、Samala Mallesham

  DOI：10.1016/j.tetasy.2010.10.016

  日期：2010.11

  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