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-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol | 1169754-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 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-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
• 英文别名: [(2R,3S,4R)-3-acetyloxy-4-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1169754-59-9
• 化学式: C₄₈H₆₄O₃₁
• 分子量: 1137.02
• InChiKey: PQVRAJHMPPSPOC-MOFJLWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  79
• 可旋转键数：
  34
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  380
• 氢给体数：
  0
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  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-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol 在 mercury(II) diacetate 、 水 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.77h， 生成 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-D-glucopyranose
  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：

  Glc2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b1-3)a-Glc1Br2Ac4Ac6Ac 在 二氯二茂钛 、 锰 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以2.49 g的产率得到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-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol
  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