Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(S)-5-amino-5-(3-tert-butoxycarbonylamino-propylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester | 924297-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(S)-5-amino-5-(3-tert-butoxycarbonylamino-propylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester
• CAS: 924297-16-5
• 化学式: C₂₈H₄₈N₄O₁₂
• 分子量: 632.709
• InChiKey: LTJCNAJRVPPDGM-NUIZIRNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  219.91
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(S)-5-amino-5-(3-tert-butoxycarbonylamino-propylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester 、 乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以27 mg的产率得到
  参考文献：
  名称：

  Synthesis of biotinylated tumor-associated carbohydrate antigens for immunological studies

  摘要：

  Syntheses of several biotinylated human cancer-associated carbohydrate antigens for immunological studies are described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.113
• 作为产物：
  描述：

  (S)-6-((2S,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid 在 哌啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(S)-5-amino-5-(3-tert-butoxycarbonylamino-propylcarbamoyl)-pentyloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Preparation and Evaluation of Unimolecular Pentavalent and Hexavalent Antigenic Constructs Targeting Prostate and Breast Cancer:  A Synthetic Route to Anticancer Vaccine Candidates

  摘要：

  Several novel, fully synthetic, carbohydrate-based antitumor vaccines have been assembled. Each construct consists of multiple cancer-related antigens displayed on a single polypeptide backbone. Recent advances in synthetic methodology have allowed for the incorporation of a complex oligosaccharide terminating in a sialic acid residue (i.e., GM2) as one of the carbohydrate antigens. Details of the vaccine synthesis as well as the results of preliminary immunological investigations are described herein.

  DOI：

  10.1021/ja057244+