1-((4-hydroxyphenyl)acetyl)-β-D-glucopyranosylamine | 1309886-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((4-hydroxyphenyl)acetyl)-β-D-glucopyranosylamine
• 英文别名: N-β-D-glucopyranosyl-p-hydroxyphenylacetamide；N-beta-d-glucopyranosyl-p-hydroxy-phenylacetamide；2-(4-hydroxyphenyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 1309886-45-0
• 化学式: C₁₄H₁₉NO₇
• 分子量: 313.307
• InChiKey: WBCJLLACAHOLSS-RGCYKPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-((4-hydroxyphenyl)acetyl)-β-D-glucopyranosylamine 在 盐酸 、 水 作用下， 反应 7.0h， 生成 葡萄糖
  参考文献：
  名称：

  Chemical constituents of Drypetes gossweileri and their enzyme inhibitory and anti-fungal activities

  摘要：

  Phytochemical studies on themethanolic extract of Drypetes gossweileri afforded N-beta-D-glucopyranosyl-p-hydroxyphenylacetamide (1), p-hydroxyphenylacetic acid (2), p-hydroxyphenyl-acetonitrile (3), phydroxyacetophenone (4), 3,4,5-trimethoxyphenol (5), dolichandroside A (6), and beta-amyrone (7). Compounds 1-7 were identified with the aid of extensive NMR and MS spectroscopic studies. Compound 1 was a new natural product and was isolated for the first time from plant containing N-glucose moiety incorporated in its structure. Compounds 1-7 exhibited moderate to the weak source anti-alpha-glucosidase inhibitory activity. Compound 7 exhibited moderate anti-acetylcholinesterase (AChE) activity while the rest of the isolates were weakly active in this bioassay. Compounds 1-7 also showed moderate antifungal activity. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2010.10.007
• 作为产物：
  描述：

  1-((4-acetoxylphenyl)acetyl)-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)amine 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 1-((4-hydroxyphenyl)acetyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  硫脲/卤素键供体共催化用酰胺基三氯乙酰胺酸酰胺直接进行N-糖基官能化

  摘要：

  使用卤素键（XB）供体和Schreiner的硫脲作为协同催化剂，将各种酰胺（包括几种肽的天冬酰胺残基）直接与糖基三氯乙酰亚氨酸酯偶联，以高收率得到独特的N-酰基邻酰胺。还展示了N-酰基邻酰胺的合成应用，包括重排至相应的β-N-糖苷。

  DOI：

  10.1002/anie.201712726

文献信息

• Ｎ−結合型糖鎖修飾アミド化合物
  申请人：国立大学法人京都大学

  公开号：JP2018203621A

  公开（公告）日：2018-12-27

  【課題】新規なＮ−結合型糖鎖修飾アミド化合物を提供する。【解決手段】式（１）のＮ−結合型糖鎖修飾アミド化合物とする。式（１）の環状構造Ａ1は、該構造の構成原子として酸素Ｏ1、炭素Ｃ1および炭素Ｃ2を含む糖又は糖の誘導体；Ａ2はアミド化合物であり、該化合物のアミド基の窒素が炭素Ｃ3に結合し；Ａ3は糖であり存在しなくてもよく、存在する場合、構造Ａ1の構成原子に結合してＡ1と糖鎖を構成し；Ｒ1は水素、ハロゲン又は炭素Ｃ3に結合した炭素、酸素もしくは硫黄を含む基である。【選択図】図２８

  提供一种新的N-连接型糖链修饰酰胺化合物。将式（1）中的N-连接型糖链修饰酰胺化合物作为解决方案。其中，环状结构A1包括糖或糖衍生物的构成原子氧O1、碳C1和碳C2；A2是酰胺化合物，该化合物的酰胺基氮与碳C3结合；A3是糖，可以不存在，如果存在，则与结构A1的构成原子结合以形成A1和糖链；R1是氢、卤素或与碳C3、氧或硫结合的基团。【选定图】图28
• Direct <i>N</i> -Glycofunctionalization of Amides with Glycosyl Trichloroacetimidate by Thiourea/Halogen Bond Donor Co-Catalysis
  作者：Yusuke Kobayashi、Yuya Nakatsuji、Shanji Li、Seiji Tsuzuki、Yoshiji Takemoto

  DOI：10.1002/anie.201712726

  日期：2018.3.26

  Using a halogen bond (XB) donor and Schreiner's thiourea as cooperative catalysts, various amides, including the asparagine residues of several peptides, were directly coupled with glycosyl trichloroacetimidates to give unique N‐acylorthoamides in good yields. Synthetic applications of N‐acylorthoamides, including rearrangement to the corresponding β‐N‐glycoside, were also demonstrated.

  使用卤素键（XB）供体和Schreiner的硫脲作为协同催化剂，将各种酰胺（包括几种肽的天冬酰胺残基）直接与糖基三氯乙酰亚氨酸酯偶联，以高收率得到独特的N-酰基邻酰胺。还展示了N-酰基邻酰胺的合成应用，包括重排至相应的β-N-糖苷。
• Chemical constituents of Drypetes gossweileri and their enzyme inhibitory and anti-fungal activities
  作者：Athar Ata、Damaris S. Tan、Wadim L. Matochko、Julius K. Adesanwo

  DOI：10.1016/j.phytol.2010.10.007

  日期：2011.3

  Phytochemical studies on themethanolic extract of Drypetes gossweileri afforded N-beta-D-glucopyranosyl-p-hydroxyphenylacetamide (1), p-hydroxyphenylacetic acid (2), p-hydroxyphenyl-acetonitrile (3), phydroxyacetophenone (4), 3,4,5-trimethoxyphenol (5), dolichandroside A (6), and beta-amyrone (7). Compounds 1-7 were identified with the aid of extensive NMR and MS spectroscopic studies. Compound 1 was a new natural product and was isolated for the first time from plant containing N-glucose moiety incorporated in its structure. Compounds 1-7 exhibited moderate to the weak source anti-alpha-glucosidase inhibitory activity. Compound 7 exhibited moderate anti-acetylcholinesterase (AChE) activity while the rest of the isolates were weakly active in this bioassay. Compounds 1-7 also showed moderate antifungal activity. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.