[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1H-pyrrole-2-carbonyloxy)oxan-3-yl] 1H-pyrrole-2-carboxylate | 915720-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1H-pyrrole-2-carbonyloxy)oxan-3-yl] 1H-pyrrole-2-carboxylate
• CAS: 915720-00-2
• 化学式: C₁₆H₁₈N₂O₈
• 分子量: 366.328
• InChiKey: JIXJPVLNNSKARZ-VBTGVMJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1H-pyrrole-2-carbonyloxy)oxan-3-yl] 1H-pyrrole-2-carboxylate 在 Candida antarctica lipase 、 ammonium acetate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 buprestin B
  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
• 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 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1H-pyrrole-2-carbonyloxy)oxan-3-yl] 1H-pyrrole-2-carboxylate
  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

• Synthesis of buprestins D, E, F, G and H; structural confirmation and biological testing of acyl glucoses from jewel beetles (Coleoptera: Buprestidae)
  作者：Sebastian Ryczek、Konrad Dettner、Carlo Unverzagt

  DOI：10.1016/j.bmc.2008.12.038

  日期：2009.2

  A chemical and enzymatic synthesis was developed for five variant buprestins termed D, E, F, G and H found in jewel beetles (Coleoptera: Buprestidae). Selective acylation of the primary hydroxyl group of β-d-glucopyranose-1,2-bis(pyrrole-2-carboxylate) with substituted benzoic or cinnamic acid derivatives followed by deprotection gave the target compounds. Using coinjection the identity with the natural

  针对宝石甲虫（鞘翅目：Buprestidae）中发现的五种变种布氏抑素（Dup，E，F，G和H）进行了化学和酶促合成。β- d-吡喃葡萄糖-1,2-双（吡咯-2-羧酸酯）的伯羟基被取代的苯甲酸或肉桂酸衍生物选择性酰化，然后脱保护，得到目标化合物。通过共注射，证实了与天然提取物的同一性。测定了变种布抑素作为蚂蚁的威慑剂的活性。
• 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.