isopropyl 3-deoxy-2-oxo-6-O-dimethyl-tert-butylsilyl-4,5:7,8-di-O-isopropylidene-D-gluco-octuronate | 850182-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3-deoxy-2-oxo-6-O-dimethyl-tert-butylsilyl-4,5:7,8-di-O-isopropylidene-D-gluco-octuronate
• 英文别名: propan-2-yl 3-[(4S,5R)-5-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxopropanoate
• CAS: 850182-02-4
• 化学式: C₂₃H₄₂O₈Si
• 分子量: 474.667
• InChiKey: JYTUEHCTXSSBMF-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  isopropyl 3-deoxy-2-oxo-6-O-dimethyl-tert-butylsilyl-4,5:7,8-di-O-isopropylidene-D-gluco-octuronate 、 甲基膦酸二乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 生成 2-C-(diethoxy-phosphorylmethyl)-3-deoxy-4,5:7,8-di-O-isopropylidene-6-dimethyl-tert-butylsilyl D-glycero-D-ido-octonic acid isopropyl ester 、 2-C-(diethoxy-phosphorylmethyl)-3-deoxy-4,5:7,8-di-O-isopropylidene-6-dimethyl-tert-butylsilyl-D-glycero-D-gulo-octonic acid isopropyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase

  摘要：

  KDO8PS (3-deOXY-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deOXY-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.019
• 作为产物：
  描述：

  二氯乙酸异丙酯 在 potassium methanolate 、 magnesium iodide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 isopropyl 3-deoxy-2-oxo-6-O-dimethyl-tert-butylsilyl-4,5:7,8-di-O-isopropylidene-D-gluco-octuronate
  参考文献：
  名称：

  Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase

  摘要：

  KDO8PS (3-deOXY-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deOXY-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.019

文献信息

• Investigation into the regioselective C-deuteriation of α-keto esters
  作者：Claude Grison、Sylvain Petek、Philippe Coutrot

  DOI：10.1016/j.tet.2005.05.031

  日期：2005.7

  Results are reported on the efficient regioselective C-mono and C-dideuteriation of iodomagnesium enolates derived from alpha-ketoesters in aliphatic and glucidic series using [D-4]acetic acid as the best deuterium donor. (c) 2005 Elsevier Ltd. All rights reserved.