18-pentatriacontanyl 6-O-[5-(N,N-dimethylamino)-naphthalene-1-sulfonylamino]-6-deoxy-α-D-glucopyranosyl-(1->4)-β-D-galactopyranoside | 1357296-64-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 18-pentatriacontanyl 6-O-[5-(N,N-dimethylamino)-naphthalene-1-sulfonylamino]-6-deoxy-α-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
• 英文别名: N-[[(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-pentatriacontan-18-yloxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 1357296-64-0
• 化学式: C₅₉H₁₀₄N₂O₁₂S
• 分子量: 1065.55
• InChiKey: OGKDDONPKUIFMG-JUWOFOKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  74
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  216
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 甲酸 、 钯 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 27.0h， 生成 18-pentatriacontanyl 6-O-[5-(N,N-dimethylamino)-naphthalene-1-sulfonylamino]-6-deoxy-α-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
  参考文献：
  名称：

  Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties

  摘要：

  Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an alpha-D-glucosyl-(1 -> 4)-beta-D-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6 ''-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.11.017

文献信息

• Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties
  作者：Riccardo Di Brisco、Fiamma Ronchetti、Alfonso Mangoni、Valeria Costantino、Federica Compostella

  DOI：10.1016/j.carres.2011.11.017

  日期：2012.2

  Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an alpha-D-glucosyl-(1 -> 4)-beta-D-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6 ''-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol. (C) 2011 Elsevier Ltd. All rights reserved.