4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-(4-methoxybenzyl)-β-D-glucopyranoside | 824958-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-(4-methoxybenzyl)-β-D-glucopyranoside
• 英文别名: GlcNAc3Ac4Ac6Ac(b1-4)[Mob(-3)][Mob(-6)]GlcNAc(b)-O-Mob；[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6R)-5-acetamido-4,6-bis[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]oxy-3,4-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 824958-50-1
• 化学式: C₄₆H₅₈N₂O₁₇
• 分子量: 910.97
• InChiKey: CNOISHSMXNSQLA-JQKFACAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  65
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 sodium hydroxide 、 sodium methylate 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-methoxybenzyl 2-acetamido-2-deoxy-3,4-di-O-(4-methoxybenzyl)-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-(4-methoxybenzyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase

  摘要：

  Enzymatic glycosidation using sugar oxazolines 1-3 having a carboxylate group as glycosyl donors and compounds 4-6 as glycosyl acceptors was performed by employing a chitinase from Bacillus sp. as catalyst. All the glycosidations proceeded with full control in stereochemistry at the anomeric carbon of the donor and regio-selectivity of the acceptor. The N,N'-diacetyl-6'-O-carboxymethyl chitobiose oxazoline derivative 1 was effectively glycosidated, under catalysis by the enzyme, with methyl N,N'-diacetyl-beta-chitobioside (4), pent-4-enyl N-acetyl-beta-D-glucosaminide (5), and methyl N-acetyl-beta-D-glucosaminide (6), affording in good yields the corresponding oligosaccharide derivatives having 6-O-carboxymethyl group at the nonreducing GlcNAc residue. The N,N'-diacetyl-6-O-carboxymethylchitobiose oxazoline derivative 2 was subjected to catalysis by the enzyme catalysis; however, no glycosidated products were produced through the reactions with 4, 5, and 6. Glycosidation reactions of the beta-D-glycosyluronic(1-->4)-N-acetyl-D-glucosamine oxazoline derivative 3 proceeded with each of the glycosyl acceptors, giving rise to the corresponding oligosaccharide derivative having a GlcA residue at their nonreducing termini in good yields. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.08.016
• 作为产物：
  描述：

  p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 、 一水合肼 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-(4-methoxybenzyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase

  摘要：

  Enzymatic glycosidation using sugar oxazolines 1-3 having a carboxylate group as glycosyl donors and compounds 4-6 as glycosyl acceptors was performed by employing a chitinase from Bacillus sp. as catalyst. All the glycosidations proceeded with full control in stereochemistry at the anomeric carbon of the donor and regio-selectivity of the acceptor. The N,N'-diacetyl-6'-O-carboxymethyl chitobiose oxazoline derivative 1 was effectively glycosidated, under catalysis by the enzyme, with methyl N,N'-diacetyl-beta-chitobioside (4), pent-4-enyl N-acetyl-beta-D-glucosaminide (5), and methyl N-acetyl-beta-D-glucosaminide (6), affording in good yields the corresponding oligosaccharide derivatives having 6-O-carboxymethyl group at the nonreducing GlcNAc residue. The N,N'-diacetyl-6-O-carboxymethylchitobiose oxazoline derivative 2 was subjected to catalysis by the enzyme catalysis; however, no glycosidated products were produced through the reactions with 4, 5, and 6. Glycosidation reactions of the beta-D-glycosyluronic(1-->4)-N-acetyl-D-glucosamine oxazoline derivative 3 proceeded with each of the glycosyl acceptors, giving rise to the corresponding oligosaccharide derivative having a GlcA residue at their nonreducing termini in good yields. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.08.016