苯基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃半乳糖苷 | 278784-83-1

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃半乳糖苷
• 中文别名: 苯基3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-Β-D-吡喃半乳糖苷
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside
• 英文别名: Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-galactopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-6-phenylsulfanyl-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 278784-83-1
• 化学式: C₂₁H₂₄Cl₃NO₉S
• 分子量: 572.848
• InChiKey: AZDNCEYOFMNMSH-FQBWVUSXSA-N

物化性质

• 熔点：
  115.0 to 119.0 °C
• 沸点：
  633.1±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  苯基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃半乳糖苷 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 溶剂黄146 、 锌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 52.5h， 生成 4-methoxyphenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  扩展葡萄糖神经酰胺盒方法：在神经节苷脂 GalNAc-GM1b 全合成中的应用。

  摘要：

  研究了用于有效糖脂合成的新型环状葡萄糖神经酰胺盒受体的开发。选择对甲氧基苄基 (PMB) 基团作为葡萄糖残基 C2 和 C3 处的保护基团，目的是提高盒式受体的功能。PMB 基团的选择导致 β 选择性的丧失，这通过使用适当的系链来控制空间排列和腈溶剂效应得到纠正。为了研究接头结构对分子内糖基化β-选择性的影响，设计并制备了几种用于连接葡萄糖和神经酰胺部分的接头，即琥珀酰、戊二酰、二甲基丙二酰和邻苯二甲酰酯。琥珀酸酯接头是访问盒形式的最佳选择。

  DOI：

  10.3390/molecules181215153
• 作为产物：
  描述：

  苯硫酚 、 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到苯基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-2-(2,2,2-三氯乙氧基甲酰氨基)-β-D-吡喃半乳糖苷
  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

• COMPOUNDS
  申请人：Costantino Paolo

  公开号：US20130315959A1

  公开（公告）日：2013-11-28

  The invention provides a synthetic C. difficile PS-II cell wall saccharide. The invention also provides a process for purifying C. difficile PS-II saccharide from C. difficile bacterial cells resulting in reduced contamination. The saccharides may be used in vaccines, particularly as conjugates with carrier proteins.

  该发明提供了一种合成的C. difficile PS-II细胞壁多糖。该发明还提供了一种从C. difficile细菌细胞中纯化C. difficile PS-II多糖的方法，从而减少污染。这些多糖可以用于疫苗，特别是作为与载体蛋白结合的共轭物。
• First Synthesis of <i>C. difficile</i> PS-II Cell Wall Polysaccharide Repeating Unit
  作者：Elisa Danieli、Luigi Lay、Daniela Proietti、Francesco Berti、Paolo Costantino、Roberto Adamo

  DOI：10.1021/ol1026188

  日期：2011.2.4

  difficile is the most commonly diagnosed cause of nosocomial diarrhea with increasing incidence and mortality among elderly and hospitalized patients. We report the first synthesis of the surface polysaccharide PS-II repeating unit and its nonphosphorylated analogue, with a linker for conjugation, via a (4 + 2) convergent approach from a common AB(D)C tetrasaccharide intermediate.

  艰难梭菌是医院内腹泻的最常见诊断原因，在老年人和住院患者中发病率和死亡率均在增加。我们报告了表面多糖PS-II重复单元及其非磷酸化类似物的首次合成，并通过（4 + 2）趋同方法从一个常见的AB（D）C四糖中间体进行缀合。
• Synthesis and anti-inflammatory activity of gold-nanoparticle bearing a dermatan sulfate disaccharide analog
  作者：Chengxiang Shang、Chao Cai、Cuixia Zhao、Yuguo Du

  DOI：10.1016/j.cclet.2017.06.010

  日期：2018.1

  Abstract A dermatan sulfate (DS) repeating disaccharide analog, α- l -idopyranosiduronate-(1 → 3)-2-amino-2-deoxy-4,6-di-O-sulfo-β- d -galactopyranoside, has been convergently synthesized and successfully applied to prepare the GAG-functionalized gold glyconanoparticle. This new material exhibited good anti-inflammatory activity which was comparable to that of the drug ibuprofen incarrageenan-induced

  摘要聚合了一种硫酸皮肤素（DS）重复二糖类似物α-1-吡喃二葡萄糖苷-（1→3）-2-氨基-2-脱氧-4,6-二-O-磺基-β-d-吡喃半乳糖苷合成并成功地用于制备GAG官能化的金糖纳米颗粒。这种新材料具有良好的抗炎活性，可与大鼠模型中布洛芬角叉菜胶诱导的爪浮肿相媲美。
• Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a
  作者：Haruka Hirose、Hideki Tamai、Chao Gao、Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Ten Feizi、Makoto Kiso

  DOI：10.1039/c5ob01744k

  日期：——

  Total syntheses of two natural sulphoglycolipids, disulphated glycosphingolipid SB1a and the structurally related monosulphated SM1a, are described. They have common glycan sequences and ceramide moieties and are associated with human epithelial carcinomas. The syntheses featured efficient glycan assembly and the glucosyl ceramide cassette as a versatile building block. The binding of the synthetic

  描述了两种天然磺基糖脂、二硫酸化鞘糖脂 SB1a 和结构相关的单硫酸化 SM1a 的全合成。它们具有共同的聚糖序列和神经酰胺部分，并且与人类上皮癌相关。该合成以高效的聚糖组装和葡萄糖基神经酰胺盒作为多功能构建块为特色。使用碳水化合物微阵列技术研究了合成磺基糖脂与癌症特异性单克隆抗体 AE3 的结合。
• A First Total Synthesis of a Hybrid‐Type Ganglioside Associated with Amyotrophic Lateral Sclerosis‐Like Disorder
  作者：Shinya Nakashima、Hiromune Ando、Akihiro Imamura、Nobuhiro Yuki、Hideharu Ishida、Makoto Kiso

  DOI：10.1002/chem.201002184

  日期：2011.1.10

  The hybrid ganglioside X1, which was identified in the bovine brain, was synthesized for the first time. Ganglioside X1 is believed to be involved in the development of amyotrophic lateral sclerosis‐like disorders in patients with neurological disorders after treatment with bovine brain gangliosides. A convergent approach using two branched glycan units, the GM2‐core trisaccharide and the lacto‐ganglio

  首次在牛脑中鉴定出了混合神经节苷脂X1。神经节苷脂X1被认为是在用牛脑神经节苷脂治疗后患有神经系统疾病的患者中发生肌萎缩性侧索硬化样疾病的发展。使用两个支链的聚糖单位，GM2核三糖和乳糖ganglio四糖的会聚方法，有效地提供神经节苷脂X1，将其用神经酰胺部分，以产生被保护的神经节苷脂偶联X1的高度支化七糖部分。整体脱保护递送了均质的神经节苷脂X1，来自患者的血清与之反应。