methyl α-L-rhamnopyranosyl-(1-2)-3-((glycer-2-yl)phosphate)-β-D-galactopyranoside | 1256151-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-L-rhamnopyranosyl-(1-2)-3-((glycer-2-yl)phosphate)-β-D-galactopyranoside
• 英文别名: methyl 2-O-(alpha-L-rhamnopyranosyl)-3-O-{[(1,3-dihydroxypropan-2-yl)oxy](hydroxy)phosphoryl}-beta-D-galactopyranoside；1,3-dihydroxypropan-2-yl [(2R,3S,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-methoxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl] hydrogen phosphate
• CAS: 1256151-60-6
• 化学式: C₁₆H₃₁O₁₅P
• 分子量: 494.387
• InChiKey: JTMSDJZWIOBZIQ-DTNMLCCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  methyl α-L-rhamnopyranosyl-(1-2)-3-((1,3-O-benzylideneglycer-2-yl)phosphate)-β-D-galactopyranoside 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到methyl α-L-rhamnopyranosyl-(1-2)-3-((glycer-2-yl)phosphate)-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