methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside | 697298-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside
• 英文别名: (2R,3R,4S,5S)-2-[2-[diethoxy(oxido)phosphaniumyl]ethyl]-5-methoxy-3,4-bis(phenylmethoxy)oxolane
• CAS: 697298-49-0
• 化学式: C₂₅H₃₅O₇P
• 分子量: 478.522
• InChiKey: WDWNSYOBGUBVFB-NGSHPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside 在 三甲基溴硅烷 、 氨 、 水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 24.5h， 以100%的产率得到methyl 2,3-di-O-benzyl-5-deoxy-5-phosphonomethyl-α-D-arabinofuranoside bis(ammonium) salt
  参考文献：
  名称：

  Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-d-erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase

  摘要：

  4-deoxy-4-Phosphonomethyl-D-erythronate, an isosteric and hydrolytically stable analogue of the known ribose-5-phosphate isomerase inhibitor 4-deoxy-4-phospho-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a phosphate isomerase inhibitor 4-deoxy-4-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a highly improved Synthesis of the precursor 5-deoxy-5-phosphonomethyl-D-arabinose. The title compound appears as the first stable and potent competitive inhibitor of the enzyme catalyzed isomerization of ribose-5-phosphate to D-ribulose-5-phosphate (K-i = 74 muM. K-m/K-i = 100). exhibiting only a 3-fold weaker inhibitory activity than its phosphate analogue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.004
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 在 platinum(IV) oxide 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-d-erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase

  摘要：

  4-deoxy-4-Phosphonomethyl-D-erythronate, an isosteric and hydrolytically stable analogue of the known ribose-5-phosphate isomerase inhibitor 4-deoxy-4-phospho-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a phosphate isomerase inhibitor 4-deoxy-4-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a highly improved Synthesis of the precursor 5-deoxy-5-phosphonomethyl-D-arabinose. The title compound appears as the first stable and potent competitive inhibitor of the enzyme catalyzed isomerization of ribose-5-phosphate to D-ribulose-5-phosphate (K-i = 74 muM. K-m/K-i = 100). exhibiting only a 3-fold weaker inhibitory activity than its phosphate analogue. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.004

文献信息

• Stereoselective synthesis of 5-methylphosphono-D-arabino hydroximolactone, inhibitor of glucosamine-6-phosphate synthase and phosphoglucose isomerase
  作者：Corentin Le Camus、Alexia Chassagne、Marie-Ange Badet-Denisot、Bernard Badet

  DOI：10.1016/s0040-4039(97)10514-7

  日期：1998.1

  Compound 2, synthesized from D-arabinose in 12 steps with an overall 4% yield, is a competitive inhibitor vs fructose-6P for both phosphoglucose isomerase and glucosamine-6P synthase. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-d-erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase
  作者：Emmanuel Burgos、Laurent Salmon

  DOI：10.1016/j.tetlet.2004.03.004

  日期：2004.4

  4-deoxy-4-Phosphonomethyl-D-erythronate, an isosteric and hydrolytically stable analogue of the known ribose-5-phosphate isomerase inhibitor 4-deoxy-4-phospho-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a phosphate isomerase inhibitor 4-deoxy-4-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through a highly improved Synthesis of the precursor 5-deoxy-5-phosphonomethyl-D-arabinose. The title compound appears as the first stable and potent competitive inhibitor of the enzyme catalyzed isomerization of ribose-5-phosphate to D-ribulose-5-phosphate (K-i = 74 muM. K-m/K-i = 100). exhibiting only a 3-fold weaker inhibitory activity than its phosphate analogue. (C) 2004 Elsevier Ltd. All rights reserved.