2-methyl-[3,6-di-O-acetyl-1,2-di-deoxy-4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyrano]-[2,1-d]-2-oxazoline | 824958-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-[3,6-di-O-acetyl-1,2-di-deoxy-4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyrano]-[2,1-d]-2-oxazoline
• CAS: 824958-69-2
• 化学式: C₂₅H₃₃NO₁₆
• 分子量: 603.534
• InChiKey: NBXLUPCCUZMWFG-PSUXIWLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  207.08
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-methyl-[3,6-di-O-acetyl-1,2-di-deoxy-4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyrano]-[2,1-d]-2-oxazoline 在 Carbonate buffer 、 chitinase from Bacillus sp 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 methyl (sodium β-D-glucopyranosyluronate)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-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：

  (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 10.0h， 生成 2-methyl-[3,6-di-O-acetyl-1,2-di-deoxy-4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-α-D-glucopyrano]-[2,1-d]-2-oxazoline
  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