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 | 1169754-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 1169754-63-5
• 化学式: C₅₄H₆₉NO₃₄
• 分子量: 1276.13
• InChiKey: PSJYDIPDEWSOLC-MRHYJYMGSA-N

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  对硝基苯酚 、 在 15-冠醚-5 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以291 mg的产率得到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
  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