(alphaR)-alpha-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯乙酰胺 | 207512-68-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (alphaR)-alpha-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯乙酰胺
• 英文名称: (R)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy(phenyl)acetamide
• 英文别名: (Alphar)-alpha-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]benzeneacetamide；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(1R)-2-amino-2-oxo-1-phenylethoxy]oxan-2-yl]methyl acetate
• CAS: 207512-68-3
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: QXCHUKFHDDLXBX-MRVGAPFNSA-N

物化性质

• 沸点：
  582.9±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (alphaR)-alpha-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯乙酰胺 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile
  参考文献：
  名称：

  Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.

  摘要：

  通过糖基化、羧酰胺脱水形成氰醇以及脱保护的三步反应，描述了从 O-(2,3,4,6-O-四乙酰基-α-D-吡喃葡萄糖基)三氯噻嗪酸和相应的 α-羟基酰胺合成氰苷（R）-普鲁纳辛、亚麻酰胺和（S）-heterodendrin 的简便合成路线。

  DOI：

  10.1271/bbb.62.453
• 作为产物：
  描述：

  2-羟基-2-苯基乙酰胺 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 以70%的产率得到(alphaR)-alpha-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯乙酰胺
  参考文献：
  名称：

  Facile Synthesis of Cyanogen Glycosides (R)-Prunasin, Linamarin and (S)-Heterodendrin.

  摘要：

  通过糖基化、羧酰胺脱水形成氰醇以及脱保护的三步反应，描述了从 O-(2,3,4,6-O-四乙酰基-α-D-吡喃葡萄糖基)三氯噻嗪酸和相应的 α-羟基酰胺合成氰苷（R）-普鲁纳辛、亚麻酰胺和（S）-heterodendrin 的简便合成路线。

  DOI：

  10.1271/bbb.62.453

文献信息

• Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates
  作者：Noriyuki Nakajima、Miho Saito、Makoto Ubukata

  DOI：10.1016/s0040-4020(02)00304-6

  日期：2002.4

  Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)(2)-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields. (C) 2002 Elsevier Science 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.