buprestin A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: buprestin A
• 英文别名: [(2R,3S,4S,5R,6S)-3,4-dihydroxy-5,6-bis(1H-pyrrole-2-carbonyloxy)oxan-2-yl]methyl 1H-pyrrole-2-carboxylate
• 化学式: C₂₁H₂₁N₃O₉
• 分子量: 459.412
• InChiKey: PEWLFUFCUXJGIA-IALVOCICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl glucopyranose 在 4-二甲氨基吡啶 、 Candida antarctica lipase 、 三氟化硼乙醚 、 ammonium acetate 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 buprestin A
  参考文献：
  名称：

  Chemical and enzymatic synthesis of buprestin A and B—bitter acylglucosides from Australian jewel beetles (Coleoptera: Buprestidae)

  摘要：

  A chemical and enzymatic synthesis was developed for buprestin A and B originally isolated from Australian jewel beetles (Coleoptera: Buprestidae). The common motif of both acylglucosides is a beta-D-glucopyranose-1,2-bis(pyrrole-2-carboxylate). Starting from 1,3,4,6-tetra-O-acetyl-alpha-D-glucose, the first pyrrole-2-carboxylate was introduced by DCC-DMAP mediated esterification. After conversion to a trichloroacetimidate the anomeric pyrrole-2-carboxylate was installed. Selective removal of the acetates was accomplished using immobilized Candida antarctica lipase. The resulting triol was converted to Buprestin A or B via a Mitsunobu reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.119

文献信息

• Chemical and enzymatic synthesis of buprestin A and B—bitter acylglucosides from Australian jewel beetles (Coleoptera: Buprestidae)
  作者：Sabine Schramm、Konrad Dettner、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2006.08.119

  日期：2006.10

  A chemical and enzymatic synthesis was developed for buprestin A and B originally isolated from Australian jewel beetles (Coleoptera: Buprestidae). The common motif of both acylglucosides is a beta-D-glucopyranose-1,2-bis(pyrrole-2-carboxylate). Starting from 1,3,4,6-tetra-O-acetyl-alpha-D-glucose, the first pyrrole-2-carboxylate was introduced by DCC-DMAP mediated esterification. After conversion to a trichloroacetimidate the anomeric pyrrole-2-carboxylate was installed. Selective removal of the acetates was accomplished using immobilized Candida antarctica lipase. The resulting triol was converted to Buprestin A or B via a Mitsunobu reaction. (c) 2006 Elsevier Ltd. All rights reserved.