4-nitrophenyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-2-deoxy-β-D-glucopyranoside | 718639-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-2-deoxy-β-D-glucopyranoside
• 英文别名: Glc(b1-4)Glc(b1-4)Glc(b1-3)2-deoxy-D-araHex(b)-O-Ph(4-NO2)；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[(2R,3S,4R,6S)-3-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 718639-60-2
• 化学式: C₃₀H₄₅NO₂₂
• 分子量: 771.681
• InChiKey: PCYNIJMMDZIXDW-MANZWDAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  362
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  4-nitrophenyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 13.5h， 生成 4-nitrophenyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an aryl 2-deoxy-β-glycosyl tetrasaccharide to probe retaining endo-glycosidase mechanism

  摘要：

  The synthesis of the 1,3-1,4-beta-glucanase substrate analogue 4-nitrophenyl O-beta-D-glucopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 4)-O-beta-D-glucopyranosyl-(1 -> 3)-2-desoxi-beta-D-glucopyranoside 2 is reported. Starting from the main tetrasaccharide obtained by enzymatic depolymerization of barley beta-glucan, the synthetic scheme involves preparation of the Corresponding 3-O-substituted glycal which was converted into a 2-deoxy-alpha-glycosyl iodide as a glycosyl donor. The key glycosylation step was successfully achieved by nucleophilic substitution of the iodide donor with 4-nitrophenolate with high beta-selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.008