2,5-anhydro-D-glucityl phosphonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-D-glucityl phosphonic acid
• 英文别名: [(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methylphosphonic acid
• 化学式: C₆H₁₃O₇P
• 分子量: 228.139
• InChiKey: DFYLWBCXEJFDNK-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(3aR,5R,6R,6aS)-6-acetyloxy-2-ethoxy-2-oxido-3a,5,6,6a-tetrahydro-3H-furo[2,3-d]oxaphosphol-2-ium-5-yl]methyl acetate 在 sodium hydroxide 、 乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 2,5-anhydro-D-glucityl phosphonic acid
  参考文献：
  名称：

  Synthesis of sugar-derived phostones by activation of γ-hydroxyphosphonic acids

  摘要：

  Treatment of carbohydrate-derived gamma-hydroxyphosphonic acids under usual acetylation conditions affords the corresponding phostones in good yield. The method could be used for the preparation of free phostones as well as alpha- and beta-phosphonomethylarabinose. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00240-5

文献信息

• Synthesis and Antituberculosis Activity of <i>C</i>-Phosphonate Analogues of Decaprenolphosphoarabinose, a Key Intermediate in the Biosynthesis of Mycobacterial Arabinogalactan and Lipoarabinomannan
  作者：Charla A. Centrone、Todd L. Lowary

  DOI：10.1021/jo026247r

  日期：2002.12.1

  arabinosyltransferases that use decaprenolphosphoarabinose (3) as the donor species. In this paper, we describe the synthesis of a panel of C-phosphonate analogues of 3, which were designed to inhibit these arabinosyltransferases and thus block the biosynthesis of mycobacterial cell wall polysaccharides. A number of routes were explored for the preparation of the targets. The successful approach involved the

  分枝杆菌中的细胞壁复合物，包括人类病原体结核分枝杆菌，大部分包含在两种多糖中，其中含有大量的阿拉伯呋喃糖残基。这两种多糖都是由阿拉伯糖基转移酶家族组装而成的，这些家族使用癸癸醇磷酸阿拉伯糖（3）作为供体。在本文中，我们描述了一组3的C-膦酸酯类似物的合成，旨在抑制这些阿拉伯糖基转移酶，从而阻止分枝杆菌细胞壁多糖的生物合成。探索了许多路线以准备目标。成功的方法涉及合成保护的C-膦酸酯烯丙基酯16，然后通过烯烃交叉复分解反应将其偶联到烯烃上。随后用二酰亚胺还原烯烃并脱保护得到目标。这些化合物在体外针对结核分枝杆菌的筛选显示，其中一种化合物15f具有抗结核活性，MIC值为3.13 microg / mL。
• Antidiabetic phosphonates
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0372157A1

  公开（公告）日：1990-06-13

  Phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, therey lowering glu­cose levels in mammals. These phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphonates are also dis­closed.

  已公开的膦酸盐可刺激果糖-1,6-二磷酸酶并抑制 6-磷酸果糖-1-激酶，从而降低哺乳动物体内的葡萄糖水平。因此，这些膦酸盐可用于治疗高血糖和/或糖尿病。此外，还公开了膦酸盐的合成工艺。
• US4945158A
  申请人：——

  公开号：US4945158A

  公开（公告）日：1990-07-31
• Synthesis of sugar-derived phostones by activation of γ-hydroxyphosphonic acids
  作者：Michaël Bosco、Philippe Bisseret、Jacques Eustache

  DOI：10.1016/s0040-4039(03)00240-5

  日期：2003.3

  Treatment of carbohydrate-derived gamma-hydroxyphosphonic acids under usual acetylation conditions affords the corresponding phostones in good yield. The method could be used for the preparation of free phostones as well as alpha- and beta-phosphonomethylarabinose. (C) 2003 Elsevier Science Ltd. All rights reserved.