(R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide | 66427-91-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide
• 英文别名: amygdalin amide；(R)-amygdalin amide；(2R)-2-[6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyloxy]phenyl-acetamide；O-beta-D-Gentiobiosyl-D-(-)-mandelamide；(2R)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetamide
• CAS: 66427-91-6
• 化学式: C₂₀H₂₉NO₁₂
• 分子量: 475.45
• InChiKey: OCQMNDCGKQJTNY-BFMJJVGDSA-N

物化性质

• 沸点：
  800.0±60.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  222
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide 在 吡啶 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以20 mg的产率得到苦杏仁苷
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cyanogenic Glycosides

  摘要：

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

  DOI：

  10.1080/07328303.2015.1105249
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)trichloroacetimidate 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide
  参考文献：
  名称：

  Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

  摘要：

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.071

文献信息

• Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T
  作者：Eyleen Araya、Alex Rodriguez、Jaime Rubio、Alessandro Spada、Jesus Joglar、Amadeu Llebaria、Carmen Lagunas、Andres G. Fernandez、Susanna Spisani、Juan J. Perez

  DOI：10.1016/j.bmcl.2004.12.071

  日期：2005.3

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Cyanogenic Glycosides
  作者：Dmitry V. Yashunsky、Ekaterina V. Kulakovskaya、Tatiana V. Kulakovskaya、Olga S. Zhukova、Mikhail V. Kiselevskiy、Nikolay E. Nifantiev

  DOI：10.1080/07328303.2015.1105249

  日期：2015.10.13

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.