p-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside | 475987-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: 4-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside；4-Methoxyphenyl 3,4,6-tri-O-benzoyl-beta-D-galactopyranoside；[(2R,3S,4R,5R,6S)-3,4-dibenzoyloxy-5-hydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 475987-13-4
• 化学式: C₃₄H₃₀O₁₀
• 分子量: 598.606
• InChiKey: FFWHEZDOUADLTQ-CXIBEGASSA-N

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：

  苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 、 p-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.5h， 以96%的产率得到4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa

  摘要：

  The glycosphingolipid neurosporaside (alpha-D-Glcp-(1 -> 2)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 ->)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.018
• 作为产物：
  描述：

  4-Methoxyphenyl 2-O-allyl-3,4,6-tri-O-benzoyl-beta-D-galactopyranoside 在 氯化钯 EtOAc-hexanes 、 氯仿 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以gave product 5 (39 mg, 92%.) [α]D2=+78.2° (c=0.1, CHCl3)的产率得到p-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Antigen Constructs Against Campylobacter Jejuni

  摘要：

  本发明涉及一种免疫原性合成构造体，其能够诱导受体内的一种或多种单糖含有一种或多种MeOPN基团，从而诱导对弯曲菌（C. jejuni）的免疫反应。具体而言，本发明涉及一种免疫原性合成构造体，其能够诱导受体内的一种或多种MeOPN→6 Gal单糖含有对弯曲菌（C. jejuni）的免疫反应。本发明还涉及包含该免疫原性合成构造体的组合物以及诱导受体对C. jejuni进行免疫反应的方法，包括向受体注射该免疫原性合成构造体和/或包含该免疫原性合成构造体的组合物。

  公开号：

  US20160144017A1

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
• Regioselective benzoylation of sugars mediated by excessive Bu2SnO: observation of temperature promoted migration
  作者：Zhiyuan Zhang、Chi-Huey Wong

  DOI：10.1016/s0040-4020(02)00661-0

  日期：2002.8

  Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including galactosides, glucosides, mannosides and lactosides in high yields. These compounds are useful as building blocks for the synthesis of complex saccharides and derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US9925254B2
  申请人：——

  公开号：US9925254B2

  公开（公告）日：2018-03-27
• Synthesis of a new glycosphingolipid, neurosporaside, from Neurospora crassa
  作者：Isao Ohtsuka、Noriyasu Hada、Misaki Kanemaru、Takanari Fujii、Toshiyuki Atsumi、Nobuko Kakiuchi

  DOI：10.1016/j.carres.2014.11.018

  日期：2015.3

  The glycosphingolipid neurosporaside (alpha-D-Glcp-(1 -> 2)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 ->)-Cer) occurs in Neurospora crassa. We attempted to synthesize neurosporaside by block synthesis (route A) and linear synthesis (route B). Oligosaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfonate and N-iodosuccinimide/trifluoromethane sulfonic acid as promoters. The target tetrasaccharide could not be attained via route A, but route B showed potential: glycosidic bonds (beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp) were formed stereoselectively, leading to the synthesis of glycosphingolipid 2. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthetic Antigen Constructs Against Campylobacter Jejuni
  申请人：Guerry Patricia

  公开号：US20160144017A1

  公开（公告）日：2016-05-26

  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 Campylobacter jejuni ( C. jejuni ) in a subject comprising one or more MeOPN→6 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 construct, to the subject.

  本发明涉及一种免疫原性合成构造体，其能够诱导受体内的一种或多种单糖含有一种或多种MeOPN基团，从而诱导对弯曲菌（C. jejuni）的免疫反应。具体而言，本发明涉及一种免疫原性合成构造体，其能够诱导受体内的一种或多种MeOPN→6 Gal单糖含有对弯曲菌（C. jejuni）的免疫反应。本发明还涉及包含该免疫原性合成构造体的组合物以及诱导受体对C. jejuni进行免疫反应的方法，包括向受体注射该免疫原性合成构造体和/或包含该免疫原性合成构造体的组合物。