o-aminobenzyl β-D-glucopyranoside | 1581692-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-aminobenzyl β-D-glucopyranoside
• 英文别名: iteamine；(2R,3R,4S,5S,6R)-2-[(2-aminophenyl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1581692-99-0
• 化学式: C₁₃H₁₉NO₆
• 分子量: 285.297
• InChiKey: BQRRQISPSWTJIH-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-Nitrobenzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.33h， 生成 o-aminobenzyl β-D-glucopyranoside
  参考文献：
  名称：

  Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence

  摘要：

  Iteamine, o-aminobenzyl beta-D-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of D-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver alpha-N-acetylgalactosaminidase. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.01.012

文献信息

• Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence
  作者：Benjamin J. Ayers、Jacqueline Hollinshead、Alexander W. Saville、Shinpei Nakagawa、Isao Adachi、Atsushi Kato、Ken Izumori、Barbara Bartholomew、George W.J. Fleet、Robert J. Nash

  DOI：10.1016/j.phytochem.2014.01.012

  日期：2014.4

  Iteamine, o-aminobenzyl beta-D-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of D-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver alpha-N-acetylgalactosaminidase. (C) 2014 Elsevier Ltd. All rights reserved.