phenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-1-thio-α-D-ribo-hexopyranoside | 278784-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-1-thio-α-D-ribo-hexopyranoside
• 英文别名: phenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-α-D-ribo-1-thiohexopyranoside；[(2R,3R,5S,6R)-6-methyl-5-phenylmethoxy-2-phenylsulfanyloxan-3-yl] 2,2-dimethylpropanoate
• CAS: 278784-78-4
• 化学式: C₂₄H₃₀O₄S
• 分子量: 414.566
• InChiKey: JODPXXQXCUOLEV-XYEHWOGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-1-thio-α-D-ribo-hexopyranoside 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 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 13.5h， 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 、 三氟化硼乙醚 、 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 158.75h， 生成 phenyl 4-O-benzyl-3,6-dideoxy-2-O-pivaloyl-1-thio-α-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

• Synthesis of disaccharide congeners of the <i>Trichinella spiralis</i> glycan and binding site mapping of two monoclonal antibodies
  作者：Ping Zhang、Judith Appleton、Chang-Chun Ling、David R Bundle

  DOI：10.1139/v02-117

  日期：2002.8.1

  The tetrasaccharide epitope, β-D-Tyvp(1[Formula: see text]3)β-D-GalNAcp(1[Formula: see text]4)[α-L-Fucp(1[Formula: see text]3)]β-D-GlcNAcp (1) is the major constituent of the N-glycan expressed on the cell surface of the parasite Trichinella spiralis. Two monoclonal antibodies (Mabs 9D4 and 18H1) that protect rats against infection by T. spiralis bind the terminal disaccharide epitope β-D-Tyvp(1[Formula: see text]3)β-D-GalNAcp conjugated to BSA. The syntheses of disaccharide congeners containing mono-deoxy, mono-methyl, as well as modifications to replace the acetamido group are reported. These target disaccharides were assayed for binding to the protective MAbs. For each antibody different clusters of three hydroxyl groups, that include C-2 and C-4 of tyvelose and for 18H1, the GalNAc acetamido group, provide the key polar interactions with the antibody binding sites. Mapping of the sites by functional group replacement revealed a similar pattern of recognition for the dideoxyhexose by the two MAbs while each recognizes distinct surfaces of the GalNAc residue. Consequently although both antibodies bury the 4-OH of tyvelose, the principal contact surface occurs on opposite sides of the 3,6-dideoxyhexose.Key words: β-tyveloside, 3,6-dideoxy-D-arabino-hexose, Trichinella carbohydrate antigen, antibody mapping, Trichinella spiralis, N-glycans, molecular recognition of carbohydrates, antigen topology, functional group replacement.

  四糖基表位，β-D-Tyvp（1 [Formula：see text] 3）β-D-GalNAcp（1 [Formula：see text] 4）[α-L-Fucp（1 [Formula：see text] 3）]β-D-GlcNAcp（1）是寄生虫旋毛虫细胞表面表达的N-糖基的主要成分。两种单克隆抗体（Mabs 9D4和18H1）能保护大鼠免受旋毛虫感染，它们结合到与BSA结合的终端二糖基表位β-D-Tyvp（1 [Formula：see text] 3）β-D-GalNAcp。报道了含有单脱氧，单甲基以及替换乙酰胺基团的修饰的二糖类似物的合成。对这些靶向二糖的结合进行了保护MAbs的测定。对于每种抗体，包括tyvelose的C-2和C-4以及18H1的GalNAc乙酰胺基团的三个羟基团簇提供了与抗体结合位点的关键极性相互作用。通过功能团替换的映射表明，两种MAbs对于二脱氧己糖的识别模式相似，而每种MAbs都识别GalNAc残基的不同表面。因此，尽管两种抗体都掩埋了tyvelose的4-OH，但主要接触表面出现在3,6-二脱氧己糖的相反侧。 关键词：β-tyveloside，3,6-二脱氧-D-阿拉伯糖，旋毛虫糖原抗原，抗体映射，旋毛虫，N-糖基，碳水化合物的分子识别，抗原拓扑，功能团替换。
• 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.