3-β-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-sitosterol | 1218785-15-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-β-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-sitosterol
• 英文别名: leonuroside A；N-[(2R,3R,4R,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1218785-15-9
• 化学式: C₃₇H₆₃NO₆
• 分子量: 617.91
• InChiKey: HLGRVFMFOATGKQ-IFFXCGBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-β-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-sitosterol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 β-glucosamine hydrochloride 、 植物甾醇
  参考文献：
  名称：

  Leonurosides A–D: Steroid N-acetylglucosaminides from the fruits of Leonurus japonicus

  摘要：

  Four new naturally occurring steroidal glycosides (leonurosides A-D, 1-4) were isolated from the dried fruits of Leonurus japonicus (motherwort fruit). Their structures were established by spectroscopic and chemical methods. The monosaccharide unit was identified to be a 2-acetamido-2-deoxy-beta-D-glucose and the aglycone is either a common 3 beta-stigmasterol or 3 beta-ergosterol derivative. These compounds are the first representatives of steroid N-acetylglucosaminides from vascular plants. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.10.016
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 吡啶 、 4-二甲氨基吡啶 、 氢溴酸 、 sodium methylate 、 silver perchlorate 、 乙酸酐 、 一水合肼 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 正丁醇 为溶剂， 反应 41.0h， 生成 3-β-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-sitosterol
  参考文献：
  名称：

  Grover, Parul; Singh, Jitender; Dhar, Journal of the Indian Chemical Society, 2009, vol. 86, # 10, p. 1112 - 1114

  摘要：

  DOI：

文献信息

• Grover, Parul; Singh, Jitender; Dhar, Journal of the Indian Chemical Society, 2009, vol. 86, # 10, p. 1112 - 1114
  作者：Grover, Parul、Singh, Jitender、Dhar、Mehta, Lovekesh

  DOI：——

  日期：——
• Leonurosides A–D: Steroid N-acetylglucosaminides from the fruits of Leonurus japonicus
  作者：Miao Ye、Guang-Lei Ma、Jing-Jing Su、Juan Xiong、Jin-Feng Hu

  DOI：10.1016/j.phytol.2014.10.016

  日期：2014.12

  Four new naturally occurring steroidal glycosides (leonurosides A-D, 1-4) were isolated from the dried fruits of Leonurus japonicus (motherwort fruit). Their structures were established by spectroscopic and chemical methods. The monosaccharide unit was identified to be a 2-acetamido-2-deoxy-beta-D-glucose and the aglycone is either a common 3 beta-stigmasterol or 3 beta-ergosterol derivative. These compounds are the first representatives of steroid N-acetylglucosaminides from vascular plants. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.