4-methoxybenzyl 2-deoxy-3,6-di-O-(4-methoxybenzyl)-2-phthalimido-β-D-glucopyranoside | 824958-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxybenzyl 2-deoxy-3,6-di-O-(4-methoxybenzyl)-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-hydroxy-2,4-bis[(4-methoxyphenyl)methoxy]-6-[(4-methoxyphenyl)methoxymethyl]oxan-3-yl]isoindole-1,3-dione
• CAS: 824958-48-7
• 化学式: C₃₈H₃₉NO₁₀
• 分子量: 669.728
• InChiKey: GMYGNBNVGVZLCU-IRJXWVIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 2-deoxy-3,6-di-O-(4-methoxybenzyl)-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 一水合肼 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4-methoxybenzyl 2-acetamido-2-deoxy-3,4-di-O-(4-methoxybenzyl)-6-O-(4-methoxytrityl)-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 camphor-10-sulfonic acid 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 4-methoxybenzyl 2-deoxy-3,6-di-O-(4-methoxybenzyl)-2-phthalimido-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