4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside | 312957-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside；4-Methoxyphenyl 2,3,6-tri-o-benzoyl-beta-d-galactopyranoside；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 312957-72-5
• 化学式: C₃₄H₃₀O₁₀
• 分子量: 598.606
• InChiKey: RAUGZJSVWAZOTP-OQTLJYCLSA-N

物化性质

• 沸点：
  758.7±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 21.0h， 生成 2,3,6-tri-O-benzoyl-4-O-levulinoyl-α-D-galactopyranosyl 2,2,2-trichloroacetimidate
  参考文献：
  名称：

  一种新的糖基化方法。第2部分：研究胶体相中金纳米颗粒上碳水化合物的延伸率

  摘要：

  已经开发了使用金胶体纳米颗粒（GCNP）合成碳水化合物延长寡糖的新反应。通过用30,31-dithia-3,6,9,12,15,18,43,46,49,52,55,58-dodecaoxa-1还原四氯金酸来制备胶体相合成中的金核，60-六十六碳二烯二醇。所提供的链烷乙炔基低聚乙二醇用作GCNP的稳定剂和碳水化合物的化学延伸中的连接基。这种胶体相合成具有几个优点，例如（1）每个反应中残留的试剂和糖基供体都可以通过超滤或凝胶过滤柱色谱法轻松去除，（2）无需进一步纯化，（3）反应可以无需任何预处理，即可直接通过MALDI-TOF MS进行监测。实际上，

  DOI：

  10.1016/j.tet.2007.01.011
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-1-bromo-β-D-galactopyranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 42.0h， 生成 4-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Galabiosyl供体；1,2,3,4,6-戊基-O-乙酰基-β-d-吡喃半乳糖的高效合成

  摘要：

  1,2,3,4,6-五-O-乙酰基-β-D-吡喃半乳糖转化为苯基2,3,4,6-四-O-苄基-1-硫代-β-D-吡喃半乳糖苷（5 ）和4-甲氧基苯基2,3,6-三-O-苯甲酰基-β-D-吡喃半乳糖苷（8）的产率分别为73％（两步）和58％（三步）。使用N-碘代琥珀酰亚胺-三甲基甲硅烷基三氟甲磺酸盐作为促进剂，用供体5对受体8进行糖基化，以95％的产率提供了galabioside 9（8.8 g）。以高产率提供的进一步转化可适合用作合成含半乳糖的低聚糖中的糖基供体的异源活化的加拉比苷（硫糖苷（1），三氯乙酰亚胺（2）和溴糖（3））。此处报道的几种化合物是结晶的，极大地简化了纯化过程。

  DOI：

  10.1016/s0008-6215(00)00154-3

文献信息

• Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0040-4039(03)00673-7

  日期：2003.4

  6-O-benzylidene-1-thio-β-d-galactopyranoside (15) as the donor, glycosylation of 2 gave α-linked products only, indicating that 4,6-O-benzylidenation led to α-stereoselectivity in spite of the C2 ester capable of neighboring group participation. Using 15 as the donor, glycosylation of mannose derivatives with 2- or 3-OH's, glucose with 2- or 3-OH's, galactose with 2-, or 3-, or 4-OH's, glucosamine and glucuronic

  4-甲氧基苯基2,3,6-三-O-苯甲酰基-β-d-吡喃葡萄糖苷（2）与异丙基3 - O-烯丙基-2,4,6-三-O-苯甲酰基-（9）或6的糖基化- ø -烯丙基-2,3,4-三ö苯甲酰基-1-硫代β-d吡喃半乳糖苷（7）作为供体，得到的α-和β连接混合物，而用异丙3- ö -氯乙酰基-2- ø -苯甲酰基-4,6- ö -benzylidene-（13）和异丙基3- ö -烯丙基-2- ø -苯甲酰基-4,6- ø -亚苄基-1-硫代-β-β-d吡喃半乳糖苷（15）作为供体，2的糖基化仅产生α-连接的产物，表明尽管C2酯能够相邻基团参与，但4,6- O-亚苄基化仍导致α-立体选择性。使用15作为供体，甘露糖衍生物与2-或3-OH's进行糖基化，葡萄糖与2-或3-OH's进行葡萄糖基化，半乳糖与2-或3-或4-或4-OH's进行半乳糖苷，葡糖胺和葡萄糖醛酸与4-OH进行糖基化。 ，以及带有
• Structure–activity relationships of galabioside derivatives as inhibitors of E. coli and S. suis adhesins: nanomolar inhibitors of S. suis adhesins
  作者：Jörgen Ohlsson、Andreas Larsson、Sauli Haataja、Jenny Alajääski、Peter Stenlund、Jerome S. Pinkner、Scott J. Hultgren、Jukka Finne、Jan Kihlberg、Ulf J. Nilsson

  DOI：10.1039/b416878j

  日期：——

  Four collections of Galα1-4Gal derivatives were synthesised and evaluated as inhibitors of the PapG class II adhesin of uropathogenic Escherichia coli and of the PN and PO adhesins of Streptococcus suis strains. Galabiosides carrying aromatic structures at C1, methoxyphenyl O-galabiosides in particular, were identified as potent inhibitors of the PapG adhesin. Phenylurea derivatisation at C3′ and methoxymethylation at O2′ of galabiose provided inhibitors of the S. suis strains type PN adhesin with remarkably high affinities (30 and 50 nM, respectively). In addition, quantitative structure–activity relationship models for E. coli PapG adhesin and S. suis adhesin type PO were developed using multivariate data analysis. The inhibitory lead structures constitute an advancement towards high-affinity inhibitors as potential anti-adhesion therapeutic agents targeting bacterial infections.

  合成并评估了四种Galα1-4Gal衍生物作为产尿致病大肠杆菌PapG II类粘附素及链球菌豚型（Streptococcus suis）PN和PO粘附素的抑制剂。具有芳香结构的半乳糖双糖，特别是含有甲氧基苯基的O-半乳糖双糖，被确定为PapG粘附素的强效抑制剂。在半乳糖双糖的C3'位进行苯基脲衍生化，以及在O2'位进行甲氧基甲基化，提供了对S. suis PN型粘附素具有显著高亲和力的抑制剂（分别为30和50 nM）。此外，利用多变量数据分析方法建立了针对大肠杆菌PapG粘附素和S. suis PO型粘附素的定量构效关系模型。这些抑制剂的领先结构为开发高亲和力的潜在抗粘附治疗剂以靶向细菌感染提供了进展。
• Quantitative studies of the binding of the class II PapG adhesin from uropathogenic Escherichia coli to oligosaccharides
  作者：Andreas Larsson、Jörgen Ohlsson、Karen W Dodson、Scott J Hultgren、Ulf Nilsson、Jan Kihlberg

  DOI：10.1016/s0968-0896(03)00114-7

  日期：2003.5

  Binding of the class 11 PapG adhesin, found at the tip of filamentous pili on Escherichia coli, to the carbohydrate moiety of globoseries glycolipids in the human kidney is a key step in development of pyelonephritis, a severe form of urinary tract infection. An assay based on surface plasmon resonance for quantification of the binding of the class 11 PapG adhesin to oligosaccharides has been developed. Using this assay dissociation constants ranging from 80 to 540 muM were determined for binding of the PapG adhesin to di-pentasaccharide fragments from the globoseries of glycolipids. A series of galabiose derivatives, modified at the anomeric position, O-2' or O-3', was also investigated. The anomeric position appeared to be the most promising for development of improved inhibitors of PapG-mediated adhesion of E. coli. p-Methoxyphenyl galabioside was found to be most potent (K-d = 140 muM), and binds to PapG almost as well as the Forssman pentasaccharide. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthetic Antigen Constructs Against Campylobacter Jejuni
  申请人：Guerry Patricia

  公开号：US20190167779A1

  公开（公告）日：2019-06-06

  The invention relates to immunogenic synthetic constructs capable of inducing an immune response against Campylobacter jejuni ( C. jejuni ) in a subject comprising one or more monosaccharides comprising one or more MeOPN moieties. Specifically, the invention relates to immunogenic synthetic constructs capable of inducing an immune response against C. jejuni in a subject comprising one or more MeOPN-6-Gal monosaccharides, one or more MeOPN-4-Gal monosaccharides, and/or one or more MeOPN-2-Gal monosaccharides. The invention also relates to compositions comprising the immunogenic synthetic constructs, and methods of inducing an immune response against C. jejuni in a subject comprising administering the immunogenic synthetic constructs, and/or compositions comprising the immunogenic synthetic constructs, to the subject. Methods of treating, preventing, or ameliorating a C. jejuni bacterial infection in a subject comprising administering to the subject one or more doses of immunoglobulins directed to one or more of the MeOPN moieties are also contemplated.
• Galabiosyl donors; efficient synthesis from 1,2,3,4,6-penta-O-acetyl-β- -galactopyranose
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0008-6215(00)00154-3

  日期：2000.10

  1,2,3,4,6-Penta-O-acetyl-beta-D-galactopyranose was transformed into phenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside (5) and 4-methoxyphenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranoside (8) in 73% (two steps) and 58% (three steps) yield, respectively. Glycosylation of the acceptor 8 with donor 5 using N-iodosuccinimide-trimethylsilyl trifluoromethanesulfonate as promoter furnished the

  1,2,3,4,6-五-O-乙酰基-β-D-吡喃半乳糖转化为苯基2,3,4,6-四-O-苄基-1-硫代-β-D-吡喃半乳糖苷（5 ）和4-甲氧基苯基2,3,6-三-O-苯甲酰基-β-D-吡喃半乳糖苷（8）的产率分别为73％（两步）和58％（三步）。使用N-碘代琥珀酰亚胺-三甲基甲硅烷基三氟甲磺酸盐作为促进剂，用供体5对受体8进行糖基化，以95％的产率提供了galabioside 9（8.8 g）。以高产率提供的进一步转化可适合用作合成含半乳糖的低聚糖中的糖基供体的异源活化的加拉比苷（硫糖苷（1），三氯乙酰亚胺（2）和溴糖（3））。此处报道的几种化合物是结晶的，极大地简化了纯化过程。