methyl hydrogen (RS) 3-(benzyloxycarbonylamino)-3-(methoxycarbonyl)-propylphosphonate | 208997-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl hydrogen (RS) 3-(benzyloxycarbonylamino)-3-(methoxycarbonyl)-propylphosphonate
• 英文别名: Methoxy-[4-methoxy-4-oxo-3-(phenylmethoxycarbonylamino)butyl]phosphinic acid；methoxy-[4-methoxy-4-oxo-3-(phenylmethoxycarbonylamino)butyl]phosphinic acid
• CAS: 208997-82-4
• 化学式: C₁₄H₂₀NO₇P
• 分子量: 345.289
• InChiKey: WMAZWYACPDQCHZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl hydrogen (RS) 3-(benzyloxycarbonylamino)-3-(methoxycarbonyl)-propylphosphonate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 生成 DL-methyl N,N-diethyl-{3-[(benzyloxycarbonyl)amino]-3-methoxycarbonylpropyl}-SR-phosphonamidate
  参考文献：
  名称：

  Investigation of Mechanism of Nitrogen Transfer in Glucosamine 6-Phosphate Synthase with the Use of Transition State Analogs

  摘要：

  Several structural analogs of putative tetrahedral intermediates of the reaction catalysed by the glutamine amide transfer domain of Candida albicans glucosamine 6-phosphate synthase have been designed and synthesized. Esters and amides of gamma-phosphonic and gamma-sulfonic analogs of glutamine and glutamic acid were tested as potential inhibitors of the enzyme. N-substituted amides 9 and 15 were found to be the strongest inhibitors in the series. Structure-activity relationship studies led to conclusions supporting the possibility of a direct nucleophilic attack of the glutamine amide nitrogen on an electrophilic site of the enzyme-bound fructose 6-phosphate as the most likely mechanism of nitrogen transfer in glucosamine 6-phosphate synthase. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1077
• 作为产物：
  描述：

  Methyl 4-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)butanoate 在 三乙烯二胺 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到methyl hydrogen (RS) 3-(benzyloxycarbonylamino)-3-(methoxycarbonyl)-propylphosphonate
  参考文献：
  名称：

  选择性裂解二苄基二对硝基苄基和二甲基 N 保护的氨基烷基膦酸酯中的一个酯基

  摘要：

  通过使用 DABCO（1,4-二氮杂双环（2.2.2）辛烷）选择性裂解相应二酯中的一个酯基团，有效地制备了苄基、对硝基苄基和甲基氢 N-保护的氨基烷基膦酸酯。

  DOI：

  10.1080/10426509808545456

文献信息

• Selective Cleavage of One Ester Group in Dibenzyl Di-P-Nitrobenzyl and Dimethyl N-Protected Aminoalkylphosphonates
  作者：Maria Hoffmann

  DOI：10.1080/10426509808545456

  日期：1998.2.1

  Benzyl, p-nitrobenzyl and methyl hydrogen N-protected aminoalkylphosphonates were efficiently prepared by selective cleavage of one ester group in the corresponding diesters using DABCO (1,4-diazabicyclo(2.2.2]octane).

  通过使用 DABCO（1,4-二氮杂双环（2.2.2）辛烷）选择性裂解相应二酯中的一个酯基团，有效地制备了苄基、对硝基苄基和甲基氢 N-保护的氨基烷基膦酸酯。
• Investigation of Mechanism of Nitrogen Transfer in Glucosamine 6-Phosphate Synthase with the Use of Transition State Analogs
  作者：Sławomir Milewski、Maria Hoffmann、Ryszard Andruszkiewicz、Edward Borowski

  DOI：10.1006/bioo.1997.1077

  日期：1997.10

  Several structural analogs of putative tetrahedral intermediates of the reaction catalysed by the glutamine amide transfer domain of Candida albicans glucosamine 6-phosphate synthase have been designed and synthesized. Esters and amides of gamma-phosphonic and gamma-sulfonic analogs of glutamine and glutamic acid were tested as potential inhibitors of the enzyme. N-substituted amides 9 and 15 were found to be the strongest inhibitors in the series. Structure-activity relationship studies led to conclusions supporting the possibility of a direct nucleophilic attack of the glutamine amide nitrogen on an electrophilic site of the enzyme-bound fructose 6-phosphate as the most likely mechanism of nitrogen transfer in glucosamine 6-phosphate synthase. (C) 1997 Academic Press.