1-O-allyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside | 56083-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-allyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside
• 英文别名: 1-O-Allyl 2,3,4-tri-O-benzyl-alpha-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxyoxan-2-yl]methanol
• CAS: 56083-16-0
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: OHCBJQXERNTLKZ-QBHLCAJUSA-N

物化性质

• 沸点：
  617.2±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-allyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 potassium tert-butylate 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 81.0h， 生成 2,3,4-tri-O-benzyl-D-galactono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032
• 作为产物：
  描述：

  allyl 6-O-trityl-α-D-galactopyranoside 在 三乙基硅烷 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 49.25h， 生成 1-O-allyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3

  摘要：

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。

  公开号：

  EP2851092A1

文献信息

• [EN] PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3<br/>[FR] VACCINS SYNTHÉTIQUES SANS PROTÉINE ET SANS PEPTIDE CONTRE LE STREPTOCOCCUS PNEUMONIAE DE TYPE 3
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015040140A1

  公开（公告）日：2015-03-26

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• Novel sulfofucosylacylglycerol derivatives and use thereof as medicaments
  申请人：TOYO SUISAN KAISHA, LTD

  公开号：US20020028777A1

  公开（公告）日：2002-03-07

  Novel sulfofucosylacylglycerol derivatives represented by General Formula (1): 1 where R 101 represents an acyl residue of a higher fatty acid and R 102 represents a hydrogen atom or an acyl residue of a higher fatty acid. The derivatives represented by General formula (1) are useful as a DNA polymerase inhibitor and an anticancer agent.

  由一般式（1）表示的新型磺醇富糠醛基甘油衍生物：其中R101代表高级脂肪酸的酰基残基，R102代表氢原子或高级脂肪酸的酰基残基。一般式（1）表示的衍生物可用作DNA聚合酶抑制剂和抗癌剂。
• Catalytic and highly stereoselective β-mannopyranosylation using a 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate as donor
  作者：Yingle Feng、Jie Yang、Chenglin Cai、Taotao Sun、Qi Zhang、Yonghai Chai

  DOI：10.1016/j.cclet.2022.02.071

  日期：2022.11

  An efficient and catalytic protocol for highly stereoselective construction of β-mannopyranosylation has been developed. Glycosylation of 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate with various acceptors proceeded smoothly in the presence of 5% Hg(II) at room temperature, resulting in the corresponding β-mannosides in high yield and exclusive β-stereoselectivity.

  已经开发了一种用于高度立体选择性构建β-吡喃甘露聚糖基化的高效催化方案。在室温下，5% Hg(II) 存在下，2,6-内酯桥接甘露糖基邻-己炔基苯甲酸酯与各种受体的糖基化反应顺利进行，从而以高产率和独特的β-立体选择性生成相应的β-甘露糖苷。
• Protein and peptide-free synthetic vaccines against Streptococcus pneumoniae type 3
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.

  公开号：US10052373B2

  公开（公告）日：2018-08-21

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和肽的共轭物，该共轭物由合成碳水化合物和载体分子组成，其中合成碳水化合物为肺炎链球菌3型荚膜多糖相关碳水化合物，载体分子为糖磷脂。所述共轭物及其药物组合物可用于肺炎链球菌相关疾病的免疫接种，更具体地说，可用于肺炎链球菌3型相关疾病的免疫接种。
• Carbohydrate-glycolipid conjugate vaccines
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US10588962B2

  公开（公告）日：2020-03-17

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及一类基于碳水化合物的新型疫苗的合成和生物评估领域。这种新型疫苗由多模块结构组成，可将疫苗应用于各种病原体。这种方法可以制备出针对所有表达免疫原性碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质共轭，共轭疫苗的热稳定性特别好。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。