p-methoxyphenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-β-D-ribo-hexopyranoside | 278784-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-β-D-ribo-hexopyranoside
• 英文别名: [(2S,3R,5S,6R)-2-(4-methoxyphenoxy)-6-methyl-5-phenylmethoxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 278784-77-3
• 化学式: C₂₅H₃₂O₆
• 分子量: 428.525
• InChiKey: VZTZDMKMBKZNFX-WIQPIVSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-β-D-ribo-hexopyranoside 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 、 乙酸酐 、 lithium 、 乙二胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙二胺 、 正丁醇 为溶剂， 反应 15.5h， 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：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 10percent Pd/carbon 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 磺酰氯 、 四乙基溴化铵 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 barium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~60.0 ℃ 、101.33 kPa 条件下， 反应 156.75h， 生成 p-methoxyphenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-β-D-ribo-hexopyranoside
  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

文献信息

• Efficient Synthesis of 3,6-Dideoxy-β-<scp>d</scp>-<i>a</i><i>rabino</i>-hexopyranosyl-Terminated LacdiNac Glycan Chains of the <i>Trichinella </i><i>s</i><i>piralis</i> Parasite
  作者：Mark Nitz、David R. Bundle

  DOI：10.1021/jo991812k

  日期：2000.5.1

  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.