3'-O-(p-methoxybenzyl)-D-lactal | 688317-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-O-(p-methoxybenzyl)-D-lactal
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(2R,3S,4R)-4-hydroxy-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3-yl]oxy]-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]oxane-3,5-diol
• CAS: 688317-15-9
• 化学式: C₂₀H₂₈O₁₀
• 分子量: 428.436
• InChiKey: DWZWBKMALATJRN-HGHADFFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-O-(p-methoxybenzyl)-D-lactal 在 18-冠醚-6 、 碳酸氢钠 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 (2S,3S,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-6-hydroxymethyl-tetrahydro-pyran-2,3,4-triol
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155
• 作为产物：
  描述：

  4-甲氧基氯苄 、 D-lactal 在 二正丁基氧化锡 、 cesium fluoride 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 以72%的产率得到3'-O-(p-methoxybenzyl)-D-lactal
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155

文献信息

• A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite
  作者：Dipali Ruhela、Ram A. Vishwakarma

  DOI：10.1016/j.tetlet.2004.01.155

  日期：2004.3

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.