6-chlorohexyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 278784-87-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chlorohexyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2R,3S,4R,5R,6R)-6-(6-chlorohexoxy)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 278784-87-5
• 化学式: C₄₈H₅₇ClN₂O₁₅
• 分子量: 937.438
• InChiKey: ZROQHNRMELBWSQ-MBIWEIRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  66
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  201
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6-chlorohexyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 sodium azide 、 4 Angstroem MS 、 sodium methylate 、 silver trifluoromethanesulfonate 、 乙酸酐 、 lithium 、 对甲苯磺酸 、 乙二胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙二胺 、 乙腈 、 正丁醇 为溶剂， 反应 16.83h， 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
• 作为产物：
  描述：

  6-chlorohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 盐酸 、 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 sodium methylate 、 silver trifluoromethanesulfonate 、 methyl orange 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 、 镉 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.66h， 生成 6-chlorohexyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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