2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide | 592529-48-1

• 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: 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide
• CAS: 592529-48-1
• 化学式: C₄₇H₆₀N₂O₂₀
• 分子量: 972.995
• InChiKey: JAKYTTJYMHSFMV-GJXUETGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  69.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  271.38
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide 在 palladium dihydroxide 、 manganese(ll) chloride bovine milk D-GlcNAc β-(1->4)-galactosyltransferase 、 FucT-III 、 Ni⁽²⁺⁾-Agarose 、 UDP-glucose-4-epimerase 、 水 、 氢气 、 sodium cacodylate 、 三乙胺 、 manganese(ll) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 136.0h， 生成 2,2-[O-β-D-galactopyranosyl-(1->4)-(2-amino-2-deoxy-3-O-α-L-fucopyranosyl-β-D-glucopyranosyloxy)-propane butane 1N,4N'-dioyl amide]-1,3-diol
  参考文献：
  名称：

  Chemo-enzymatic synthesis of a divalent sialyl Lewisx ligand with restricted flexibility

  摘要：

  To study the influence of the entropic factor in cluster cooperative effects, a divalent sialyl Lewis(x) ligand with restricted flexilbility was chemo-enzymatically synthesized. First, a cyclized precursor with both glucosamine residues bridged together by a succinyl group was readily obtained in 42% yield by treatment of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranosyloxy)-propane with succinyl chloride. After deacetylation, this precursor was subjected to stepwise enzymatic elongation utilizing successively, soluble galactosyltransferase, then recombinant sialyltransferase and fucosyltransferase; the latter enzymes immobilized on Ni2+-Agarose, to afford, after debenzylation, a divalent sialyl Lewis(+) ligand of restricted flexibility. in 45% overall yield. Following the same enzymatic sequence, a totally flexible ligand, required as a reference compound for evaluation of inhibitory activity toward selectins, was also prepared from 2,2(bis-benzyloxymethyl)-1,3-bis(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-propane, as well as both related divalent Lewis' molecules lacking the sialic acids, the rigid one and the flexible one. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00129-0
• 作为产物：
  描述：

  甲醇 、 丁二酰氯 、 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以42%的产率得到2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide
  参考文献：
  名称：

  Chemo-enzymatic synthesis of a divalent sialyl Lewisx ligand with restricted flexibility

  摘要：

  To study the influence of the entropic factor in cluster cooperative effects, a divalent sialyl Lewis(x) ligand with restricted flexilbility was chemo-enzymatically synthesized. First, a cyclized precursor with both glucosamine residues bridged together by a succinyl group was readily obtained in 42% yield by treatment of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranosyloxy)-propane with succinyl chloride. After deacetylation, this precursor was subjected to stepwise enzymatic elongation utilizing successively, soluble galactosyltransferase, then recombinant sialyltransferase and fucosyltransferase; the latter enzymes immobilized on Ni2+-Agarose, to afford, after debenzylation, a divalent sialyl Lewis(+) ligand of restricted flexibility. in 45% overall yield. Following the same enzymatic sequence, a totally flexible ligand, required as a reference compound for evaluation of inhibitory activity toward selectins, was also prepared from 2,2(bis-benzyloxymethyl)-1,3-bis(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-propane, as well as both related divalent Lewis' molecules lacking the sialic acids, the rigid one and the flexible one. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00129-0