methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside | 1256151-61-7

• 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)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 1256151-61-7
• 化学式: C₃₈H₅₂O₁₃Si
• 分子量: 744.909
• InChiKey: NBVZVIDPUHXVPF-JBGREGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 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)-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
• 作为产物：
  描述：

  乙基 2,3,4-三-O-乙酰基-6-脱氧-1-硫代-alpha-L-吡喃甘露糖苷 、 methyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1-2)-6-O-tert-butyldiphenylsilyl-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