6-aminohexyl (3,6-dideoxy-arabino-hexopyranosyl)(1->3)(2-acetamido-2-deoxy-β-D-galactopyranosyl)(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 278784-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-aminohexyl (3,6-dideoxy-arabino-hexopyranosyl)(1->3)(2-acetamido-2-deoxy-β-D-galactopyranosyl)(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-4-[(2S,3S,5S,6R)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(6-aminohexoxy)-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 278784-97-7
• 化学式: C₂₈H₅₁N₃O₁₄
• 分子量: 653.725
• InChiKey: OCYKMBHCPJTGIW-IIXHRCMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  261
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  异硫氰酸荧光素酯 、 6-aminohexyl (3,6-dideoxy-arabino-hexopyranosyl)(1->3)(2-acetamido-2-deoxy-β-D-galactopyranosyl)(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到6-(fluoresceinylthioureido)hexyl (3,6-dideoxy-arabino-hexopyranosyl)(1->3)(2-acetamido-2-deoxy-β-D-galactopyranosyl)(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of 3,6-Dideoxy-β-d-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

  摘要：

  The synthesis of a linear trisaccharide epitope of the Trichinella spiralis N-linked glycan, in a form amenable to glycoconjugate formation, is reported. The trisaccharide contains the synthetically challenging LacdiNAc [beta-GalpNAc(1-->4)-beta-GlcpNAc] element, as well as a terminal 3,6-dideoxy-beta-D-arabino-hexopyranose (tyvelose) residue. An orthogonal protection strategy is described, which permits the protection and manipulation of three amino groups present in the disaccharide beta-GalNAc(1-->4)-beta-GlcNAc and the tether used to prepare neoglycoconjugates. The beta-linked dideoxyhexose was generated in excellent yield by the introduction of the dideoxyhexose unit as a beta-D-ribo-hexopyranoside (paratose) followed by an oxidation-reduction sequence to generate the beta-D-arabino configuration in high diastereomeric excess. The required dideoxyhexose donor was synthesized in a series of high-yielding steps from glucose utilizing the p-methoxyphenyl glycoside.

  DOI：

  10.1021/jo991812k
• 作为产物：
  描述：

  6-氯-1-己醇 在 盐酸 、 N-碘代丁二酰亚胺 、 sodium azide 、 4 Angstroem MS 、 lutidine 、 sodium methylate 、 silver trifluoromethanesulfonate 、 methyl orange 、 乙酸酐 、 lithium 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 、 乙二胺 、 镉 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 、 乙二胺 、 N,N-二甲基甲酰胺 、 乙腈 、 正丁醇 为溶剂， 反应 24.49h， 生成 6-aminohexyl (3,6-dideoxy-arabino-hexopyranosyl)(1->3)(2-acetamido-2-deoxy-β-D-galactopyranosyl)(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of 3,6-Dideoxy-β-d-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

  摘要：

  The synthesis of a linear trisaccharide epitope of the Trichinella spiralis N-linked glycan, in a form amenable to glycoconjugate formation, is reported. The trisaccharide contains the synthetically challenging LacdiNAc [beta-GalpNAc(1-->4)-beta-GlcpNAc] element, as well as a terminal 3,6-dideoxy-beta-D-arabino-hexopyranose (tyvelose) residue. An orthogonal protection strategy is described, which permits the protection and manipulation of three amino groups present in the disaccharide beta-GalNAc(1-->4)-beta-GlcNAc and the tether used to prepare neoglycoconjugates. The beta-linked dideoxyhexose was generated in excellent yield by the introduction of the dideoxyhexose unit as a beta-D-ribo-hexopyranoside (paratose) followed by an oxidation-reduction sequence to generate the beta-D-arabino configuration in high diastereomeric excess. The required dideoxyhexose donor was synthesized in a series of high-yielding steps from glucose utilizing the p-methoxyphenyl glycoside.

  DOI：

  10.1021/jo991812k