(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-(3-Azido-propoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid | 1054678-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-(3-Azido-propoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-(3-azidopropoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 1054678-00-0
• 化学式: C₂₁H₃₅N₃O₁₇
• 分子量: 601.519
• InChiKey: JBASMTGVESZALS-GBQFWVAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  289
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-(3-Azido-propoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid 在 10percent Pd/C sodium tetrahydroborate 作用下， 以 sodium hydroxide 为溶剂， 反应 0.75h， 以17 mg的产率得到3-aminopropyl (β-D-glucopyranosyl)-(1->3)-(β-D-glucopyranosyluronic acid)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein

  摘要：

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.

  DOI：

  10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t
• 作为产物：
  描述：

  3-azidopropyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-β-D-glucopyranosyluronic acid)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-(3-Azido-propoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein

  摘要：

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.

  DOI：

  10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t