(1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-(((2R,3S,4R,5R,6S)-6-((2R,3R,4S,5S,6R)-2-(5-(benzyl(benzyloxycarbonyl)amino)pentyloxy)-3,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-(benzyloxy)-4-hydroxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-2-yl)methoxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate | 1447700-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-(((2R,3S,4R,5R,6S)-6-((2R,3R,4S,5S,6R)-2-(5-(benzyl(benzyloxycarbonyl)amino)pentyloxy)-3,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-(benzyloxy)-4-hydroxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-2-yl)methoxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate
• 英文别名: methyl (3aR,4R,6R,7aS)-3-acetyl-6-[[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[5-[benzyl(phenylmethoxycarbonyl)amino]pentoxy]-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-hydroxy-3-phenylmethoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methoxy]-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1447700-76-6
• 化学式: C₈₂H₉₄Cl₃N₃O₂₆
• 分子量: 1644.01
• InChiKey: LALIZQPIMYVPCA-QEWCAVCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  114
• 可旋转键数：
  44
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  332
• 氢给体数：
  2
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-(((2R,3S,4R,5R,6S)-6-((2R,3R,4S,5S,6R)-2-(5-(benzyl(benzyloxycarbonyl)amino)pentyloxy)-3,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-(benzyloxy)-4-hydroxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-2-yl)methoxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate 、 p-methylphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以62%的产率得到(1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-(((2R,3S,4R,5R,6S)-6-((2R,3R,4S,5S,6R)-2-(5-(benzyl(benzyloxycarbonyl)amino)pentyloxy)-3,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-(benzyloxy)-4-((4aR,6R,7R,8S)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-2-yl)methoxy)-6-(methoxycarboS28nyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate
  参考文献：
  名称：

  Synthesis and Vaccine Evaluation of the Tumor-Associated Carbohydrate Antigen RM2 from Prostate Cancer

  摘要：

  We have successfully developed a [1+2+3] one-pot strategy to synthesize the RM2 antigen hexasaccharide that was proposed to be a prostate tumor antigen. The structure of the synthetic product was verified by NMR analysis and antibody binding assay using a glycan microarray. In addition, the synthetic antigen was conjugated to a mutated diphtheria toxin (DT, CRM197) with different copy numbers and adjuvant combinations to form the vaccine candidates. After vaccination in mice, we used glycan microarrays to monitor their immune response, and the results indicated that, when one molecule of DT was incorporated with 4.7 molecules of RM2 on average (DT-RM4.7) and adjuvanted with the glycolipid C34, the combination exhibited the strongest anti-RM2 IgG titer. Moreover, the induced mouse antibodies mediated effective complement-dependent cytotoidcity (CDC) against the prostate cancer cell line LNCap.

  DOI：

  10.1021/ja403609x
• 作为产物：
  描述：

  在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以0.077 g的产率得到(1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-(((2R,3S,4R,5R,6S)-6-((2R,3R,4S,5S,6R)-2-(5-(benzyl(benzyloxycarbonyl)amino)pentyloxy)-3,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-(benzyloxy)-4-hydroxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-2-yl)methoxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate
  参考文献：
  名称：

  RM2 ANTIGENS AND USE THEREOF

  摘要：

  本文描述了合成糖基结合物、其免疫原性组合物、疫苗以及相关的工具包。本发明还提供了使用合成糖基结合物、免疫原性组合物或其疫苗来治疗和/或预防和/或诊断增殖性疾病如癌症的方法。所提供的糖基结合物包括载体和式(I-i)或式(I-ii)的糖基部分：（结构表示）。

  公开号：

  US20160193310A1

文献信息

• RM2 antigens and use thereof
  申请人：ACADEMIA SINICA

  公开号：US10086054B2

  公开（公告）日：2018-10-02

  Described herein are synthetic glycan conjugates, immunogenic compositions thereof, vaccines thereof, and kits thereof. The present invention further provides methods of using the synthetic glycan conjugates, immunogenic compositions, or vaccines thereof to treat and/or prevent and/or diagnose proliferative diseases such as cancer. The provided glycan conjugate comprises a carrier and a glycan moiety of Formula (I-i) or Formula (I-ii): (structurally represented).

  本发明描述了合成聚糖共轭物、其免疫原性组合物、疫苗及其试剂盒。本发明进一步提供了使用合成聚糖共轭物、免疫原性组合物或疫苗治疗和/或预防和/或诊断癌症等增殖性疾病的方法。所提供的聚糖共轭物包括载体和式(I-i)或式(I-ii)的聚糖分子：（结构式表示）。