dimethyl 3,4,5-tri-O-benzoyl-2,6-anhydro-D-glycero-L-gluco-heptarate | 656224-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 3,4,5-tri-O-benzoyl-2,6-anhydro-D-glycero-L-gluco-heptarate
• CAS: 656224-04-3
• 化学式: C₃₀H₂₆O₁₁
• 分子量: 562.53
• InChiKey: CLVVUYZBMADCHC-NGSHPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3,4,5-tri-O-benzoyl-2,6-anhydro-D-glycero-L-gluco-heptarate 在 sodium acetate 、 乙酸酐 作用下， 反应 1.0h， 以59%的产率得到dimethyl 4,5-di-O-benzoyl-2,6-anhydro-3-deoxy-D-xylo-hept-2-enarate
  参考文献：
  名称：

  (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

  摘要：

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.007
• 作为产物：
  描述：

  3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-gluco-heptonamide 在 铂 吡啶 、 盐酸 、 氧气 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 8.0h， 生成 dimethyl 3,4,5-tri-O-benzoyl-2,6-anhydro-D-glycero-L-gluco-heptarate
  参考文献：
  名称：

  (−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

  摘要：

  The dimethyl esters of the 2,6-anhydro-3-deoxy-hept-2-enaric acids with D-xylo, D-lyxo, L-arabino, L-lyxo- and D-ribo-configuration were synthesized from D-galactose and D-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (-)-daucic acid to have D-lyxo-configuration 46 rather than the previously assigned D-xylo stereochemistry 1. Dimethyl daucate 43 could be converted by acid-induced ring contraction and dehydration into naturally occurring (+)-osbeckic acid 47, thereby proving its (S)-configuration. Configurational identity in the pyranoid rings of (-)-daucic acid and KDO, together with available biosynthetic evidence on chelidonic acid 4, a leaf closing factor, suggests a joint, KDO 8-P-based pathway for their biosynthesis in plants. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.007