(2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid | 870279-41-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid
• 英文别名: (4S,5R)-5-[bis(phenylmethoxy)phosphoryloxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 870279-41-7
• 化学式: C₂₁H₂₅O₈P
• 分子量: 436.398
• InChiKey: YYVJXPYJAGFGNE-MOPGFXCFSA-N

物化性质

• 沸点：
  582.8±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 2.0 ℃ 、101.32 kPa 条件下， 生成
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786
• 作为产物：
  描述：

  亚磷酸三苄酯 在 吡啶 、 氢氧化钾 、 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and Evaluation of 1-Deoxy-d-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase

  摘要：

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.

  DOI：

  10.1021/jo0516786

文献信息

• Synthesis and Evaluation of 1-Deoxy-<scp>d</scp>-xylulose 5-Phosphate Analogues as Chelation-Based Inhibitors of Methylerythritol Phosphate Synthase
  作者：Joel R. Walker、C. Dale Poulter

  DOI：10.1021/jo0516786

  日期：2005.11.1

  A series of 1-deoxy-D-xylulose 5-phosphate (DXP) analogues were synthesized and evaluated as inhibitors of E. coli methylerythritol phosphate (MEP) synthase. In analogues 1-4, the methyl group in DXP was replaced by hydroxyl, hydroxylamino, methoxy, and amino moieties, respectively. In analogues 5 and 6, the acetyl moiety in DXP was replaced by hydroxymethyl and aminomethyl groups. These compounds were designed to coordinate to the active site divalent metal in MEP synthase. The carboxylate (1), methyl ester (3), amide (4), and alcohol (5) analogues were inhibitors with IC50's ranging from 0.25 to 1.0 mM. The hydroxamic acid (2) and amino (6) analogues did not inhibit the enzyme.