2-methyl-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-methoxycarbonylmethyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-di-deoxy-α-D-glucopyrano]-[2,1-d]-2-oxazoline | 824958-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-methoxycarbonylmethyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-di-deoxy-α-D-glucopyrano]-[2,1-d]-2-oxazoline
• CAS: 824958-57-8
• 化学式: C₂₇H₃₈N₂O₁₆
• 分子量: 646.603
• InChiKey: CYXBIOWBOKMXIT-LAXTVPJKSA-N

反应信息

• 作为反应物：
  描述：

  2-methyl-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-methoxycarbonylmethyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-di-deoxy-α-D-glucopyrano]-[2,1-d]-2-oxazoline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 [(2R,3S,4R,5R,6S)-5-Acetylamino-3,4-dihydroxy-6-((3aR,5R,6S,7R,7aR)-7-hydroxy-5-hydroxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-6-yloxy)-tetrahydro-pyran-2-ylmethoxy]-acetic acid methyl ester
  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：

  [(2R,3S,4R,5R,6S)-3,4-Diacetoxy-5-acetylamino-6-((2R,3S,4R,5R,6S)-4,6-diacetoxy-2-acetoxymethyl-5-acetylamino-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethoxy]-acetic acid 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 17.0h， 生成 2-methyl-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-methoxycarbonylmethyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-di-deoxy-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