methyl 6-deoxy-6-[(diethoxyphosphoryl)bromomethyl]-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-[(diethoxyphosphoryl)bromomethyl]-α-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(2-bromo-2-diethoxyphosphorylethyl)-6-methoxyoxane-3,4,5-triol
• 化学式: C₁₂H₂₄BrO₈P
• 分子量: 407.196
• InChiKey: MXZLAMPYUHOYLE-RYGBEOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-[(diethoxyphosphoryl)bromomethyl]-α-D-glucopyranoside 在 甲醇 、 水 作用下， 以 乙腈 为溶剂， 反应 23.0h， 生成 methyl 6-deoxy-6-[monobromophosphorylmethyl]-α-D-glucopyranoside bislithium salt
  参考文献：
  名称：

  α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase

  摘要：

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.003
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-glucuronic acid 在 iron(III) chloride 、 sodium tetrahydroborate 、 正丁基锂 、 nickel(II) chloride hexahydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 1.91h， 生成 methyl 6-deoxy-6-[(diethoxyphosphoryl)bromomethyl]-α-D-glucopyranoside
  参考文献：
  名称：

  α-Bromophosphonate analogs of glucose-6-phosphate are inhibitors of glucose-6-phosphatase

  摘要：

  Glucose-6-phosphatase (G6Pase) is an essential metabolic enzyme that has upregulated activity in Type II diabetes. Synthetic analogs of the G6Pase substrate, glucose-6-phosphate (G6P), may provide new tools to probe enzyme activity, or lead to specific inhibitors of glycosylphosphatase enzymes. Here we have developed synthetic routes to a panel of non-hydrolyzable G6P analogs containing alpha-bromo,alpha,alpha-dibromo, and alpha-bromo-alpha, beta-unsaturated phosphonates compatible with a carbohydrate nucleus. We confirm that these functionalities have potency as inhibitors of G6Pase in vitro, providing a series of new phosphate isosteres that can be exploited for inhibitor design. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.003