phosphoric acid dibenzyl ester 2-((2R,3R,4S,5R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethyl ester | 953812-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phosphoric acid dibenzyl ester 2-((2R,3R,4S,5R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethyl ester
• 英文别名: benzyl 6-deoxy-2,3,4-tri-O-benzyl-D-gluco-heptopyranoside 7-dibenzylphosphate
• CAS: 953812-39-0
• 化学式: C₄₉H₅₁O₉P
• 分子量: 814.912
• InChiKey: MFWDHEUVCUPOJX-ZQROTMPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.63
• 重原子数：
  59.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phosphoric acid dibenzyl ester 2-((2R,3R,4S,5R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到2-[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]ethyl dihydrogen phosphate
  参考文献：
  名称：

  Synthesis of cyclophospho-glucoses and glucitols

  摘要：

  The syntheses of cyclophosphodiesters of 5-C-(hydroxymethyl)-hexoses and hexitols and of 6-C-(hydroxymethyl)-hexoses are reported, along with that of 6-deoxy-gluco-heptose 7-phosphate. These compounds proved to be reasonable substrate mimics and show inhibitory activity against human D-myo-inositol 3-phosphate synthase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.027
• 作为产物：
  描述：

  benzyl 6-methylene-2,3,4-tri-O-benzyl-D-glucopyranoside 在 sodium hydroxide 、 双氧水 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 phosphoric acid dibenzyl ester 2-((2R,3R,4S,5R)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethyl ester
  参考文献：
  名称：

  Synthesis of cyclophospho-glucoses and glucitols

  摘要：

  The syntheses of cyclophosphodiesters of 5-C-(hydroxymethyl)-hexoses and hexitols and of 6-C-(hydroxymethyl)-hexoses are reported, along with that of 6-deoxy-gluco-heptose 7-phosphate. These compounds proved to be reasonable substrate mimics and show inhibitory activity against human D-myo-inositol 3-phosphate synthase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.027