methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-di-O-acetyl-3-triethylammonium phosphonate-β-D-galactopyranoside | 1256151-69-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-di-O-acetyl-3-triethylammonium phosphonate-β-D-galactopyranoside
• CAS: 1256151-69-5
• 化学式: C₆H₁₅N*C₂₃H₃₅O₁₇P
• 分子量: 715.686
• InChiKey: JSIQYFCCLWBTGT-RIHWBTMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  218.19
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-苯基-1,3-二氧六环-5-醇 、 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-di-O-acetyl-3-triethylammonium phosphonate-β-D-galactopyranoside 在 吡啶 、 三甲基乙酰氯 作用下， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of a core disaccharide from the Streptococcus pneumoniae type 23F capsular polysaccharide antigen

  摘要：

  The synthesis of methyl alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-galactopyranoside and methyl alpha-L-rhamnopyranosyl-(1 -> 2)-3-(glycer-2-yl-phosphate)-beta-D-galactopyranoside disaccharides from the Streptococcus pneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.002
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-di-O-acetyl-β-D-galactopyranoside 、 三乙胺 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-4,6-di-O-acetyl-3-triethylammonium phosphonate-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a core disaccharide from the Streptococcus pneumoniae type 23F capsular polysaccharide antigen

  摘要：

  The synthesis of methyl alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-galactopyranoside and methyl alpha-L-rhamnopyranosyl-(1 -> 2)-3-(glycer-2-yl-phosphate)-beta-D-galactopyranoside disaccharides from the Streptococcus pneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.002