(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 | 612844-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (2S)-6-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
• CAS: 612844-55-0
• 化学式: C₃₅H₄₂N₂O₁₃
• 分子量: 698.724
• InChiKey: KLEHKQMVJIGMSY-KJVBWLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  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+
• 作为产物：
  描述：

  (S)-6-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid benzyl ester 在 platinum on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 (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
  参考文献：
  名称：

  包含肿瘤相关碳水化合物抗原的非天然糖基氨基酸的合成

  摘要：

  描述了使用非天然氨基酸作为糖基受体的生物相关糖基氨基酸的合成。单糖三氯乙酰亚氨酸酯供体与Fmoc-1-羟基正亮氨酸苄基酯的糖基化反应提供了α- O-连接的产物。相反，当用糖基环氧供体进行糖基化反应时，β- O-连接的产物占主导。我们已经使用了这两个互补的糖基化反应来合成五个不同的糖基氨基酸，每个氨基酸都含有Tn，TF，STn，Lewis y或Globo-H肿瘤相关的碳水化合物抗原。

  DOI：

  10.1016/s0040-4020(03)00935-9

文献信息

• Synthesis of biotinylated tumor-associated carbohydrate antigens for immunological studies
  作者：Jianglong Zhu、Qian Wan、Samuel J. Danishefsky

  DOI：10.1016/j.tetlet.2008.11.113

  日期：2009.2

  Syntheses of several biotinylated human cancer-associated carbohydrate antigens for immunological studies are described. (C) 2008 Elsevier Ltd. All rights reserved.
• ‘Biologic’ level structures through chemistry: a total synthesis of a unimolecular pentavalent MUCI glycopeptide construct
  作者：Dongjoo Lee、Samuel J. Danishefsky

  DOI：10.1016/j.tetlet.2009.02.138

  日期：2009.5

  A convergent synthesis of a unimolecular pentavalent-MUC1 glycopeptide has been accomplished. A tandem repeat of unglycosylated human tumor-associated MUC1, a potential target for cancer immunotherapy, was incorporated into the known unimolecular pentavalent carbohydrate construct (5). This is an important step toward the development of a new fully synthetic anticancer vaccine candidate (1). (C) 2009 Elsevier Ltd. All rights reserved.