methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-3,4-O-isopropylidene-β-D-galactopyranoside | 1256151-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 1256151-62-8
• 化学式: C₂₂H₃₄O₁₃
• 分子量: 506.504
• InChiKey: RCBUPIJWCPUZHY-PNWLZULOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  154.51
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-3,4-O-isopropylidene-β-D-galactopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 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)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以81%的产率得到methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-3,4-O-isopropylidene-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