o-nitrobenzyl β-D-galactopyranoside | 1580000-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-nitrobenzyl β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[(2-nitrophenyl)methoxy]oxane-3,4,5-triol
• CAS: 1580000-45-8
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: PFZPMASJHPZSLG-KSSYENDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  o-nitrobenzyl β-D-galactopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以85%的产率得到o-aminobenzyl β-D-galactopyranoside
  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
• 作为产物：
  描述：

  2-nitrobenzyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以99%的产率得到o-nitrobenzyl β-D-galactopyranoside
  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

• US4629689A
  申请人：——

  公开号：US4629689A

  公开（公告）日：1986-12-16