3-{(4S,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-oxo-propionic acid methyl ester | 850182-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-{(4S,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-oxo-propionic acid methyl ester
• CAS: 850182-01-3
• 化学式: C₂₁H₃₈O₈Si
• 分子量: 446.613
• InChiKey: NWYCYFSSFMNXLV-YLFCFFPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  3-{(4S,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-oxo-propionic acid methyl ester 、 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 methyl ester 、 2-C-(diethoxy-phosphorylmethyl)-3-deoxy-4,5:7,8-di-O-isopropylidene-6-dimethyl-tert-butylsilyl-D-glycero-D-gulo-octonic acid methyl 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：

  2,3:5,6-di-O-isopropylidene-4-O-t-butyldimethylsilyl-D-glucose 在 potassium methanolate 、 magnesium iodide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3-{(4S,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-oxo-propionic acid methyl 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