Phosphoric acid dibenzyl ester 3-bromo-2,2-dimethoxy-propyl ester | 194022-79-2

• 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: Phosphoric acid dibenzyl ester 3-bromo-2,2-dimethoxy-propyl ester
• 英文别名: Phosphoric acid, 3-bromo-2,2-dimethoxypropyl bis(phenylmethyl) ester；dibenzyl (3-bromo-2,2-dimethoxypropyl) phosphate
• CAS: 194022-79-2
• 化学式: C₁₉H₂₄BrO₆P
• 分子量: 459.274
• InChiKey: MJBJVQXNQNAHQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phosphoric acid dibenzyl ester 3-bromo-2,2-dimethoxy-propyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以99%的产率得到(3-Bromo-2,2-dimethoxypropyl) dihydrogen phosphate
  参考文献：
  名称：

  A Novel Efficient Synthesis of Dihydroxyacetone Phosphate and Bromoacetol Phosphate for Use in Enzymatic Aldol Syntheses

  摘要：

  Dihydroxyacetone phosphate (DHAP, 7) and bromoacetol phosphate (BAP, 6) were synthesized in four and five steps, respectively, starting from 1,3-dibromoacetone (2). The key step involves desymetrization and ketone protection of 2 to prepare alcohol 3. Phosphorylation of 3 followed by hydrogenolysis and then deprotection of the ketal function afforded 6. A solution of 7 was prepared after treatment of 6 with NaOH. This original route allows a short and convenient preparation of DHAP in large scale and high purity for application to the synthesis of sugar derivatives and preparation of BAP for triosephosphate isomerase inhibition.

  DOI：

  10.1021/jo970565m
• 作为产物：
  描述：

  3-溴-2,2-二甲氧基-1-丙醇 、 苯甲醇 在 吡啶 、 碘 作用下， 生成 Phosphoric acid dibenzyl ester 3-bromo-2,2-dimethoxy-propyl ester
  参考文献：
  名称：

  A Novel Efficient Synthesis of Dihydroxyacetone Phosphate and Bromoacetol Phosphate for Use in Enzymatic Aldol Syntheses

  摘要：

  Dihydroxyacetone phosphate (DHAP, 7) and bromoacetol phosphate (BAP, 6) were synthesized in four and five steps, respectively, starting from 1,3-dibromoacetone (2). The key step involves desymetrization and ketone protection of 2 to prepare alcohol 3. Phosphorylation of 3 followed by hydrogenolysis and then deprotection of the ketal function afforded 6. A solution of 7 was prepared after treatment of 6 with NaOH. This original route allows a short and convenient preparation of DHAP in large scale and high purity for application to the synthesis of sugar derivatives and preparation of BAP for triosephosphate isomerase inhibition.

  DOI：

  10.1021/jo970565m

文献信息

• A Novel Efficient Synthesis of Dihydroxyacetone Phosphate and Bromoacetol Phosphate for Use in Enzymatic Aldol Syntheses
  作者：Thierry Gefflaut、Marielle Lemaire、Marie-Lise Valentin、Jean Bolte

  DOI：10.1021/jo970565m

  日期：1997.8.1

  Dihydroxyacetone phosphate (DHAP, 7) and bromoacetol phosphate (BAP, 6) were synthesized in four and five steps, respectively, starting from 1,3-dibromoacetone (2). The key step involves desymetrization and ketone protection of 2 to prepare alcohol 3. Phosphorylation of 3 followed by hydrogenolysis and then deprotection of the ketal function afforded 6. A solution of 7 was prepared after treatment of 6 with NaOH. This original route allows a short and convenient preparation of DHAP in large scale and high purity for application to the synthesis of sugar derivatives and preparation of BAP for triosephosphate isomerase inhibition.