5-(methoxycarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside | 213185-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(methoxycarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside
• 英文别名: methyl 6-[(2R,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-acetamido-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxyhexanoate
• CAS: 213185-48-9
• 化学式: C₃₃H₅₇NO₂₁
• 分子量: 803.81
• InChiKey: RVMHHOYNEXDCJL-HSNNSQOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  332
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside 在 肼 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以89%的产率得到5-(hydrazinocarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以215 mg的产率得到5-(methoxycarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a

文献信息

• Synthesis of Glycoconjugate Vaccines against <i>Shigella dysenteriae</i> Type 1
  作者：Vince Pozsgay

  DOI：10.1021/jo980660a

  日期：1998.8.1

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.