4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-tert-butyldimethylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside | 824958-61-4

• 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-6-O-tert-butyldimethylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside
• CAS: 824958-61-4
• 化学式: C₄₄H₆₄N₂O₁₆Si
• 分子量: 905.081
• InChiKey: VMTJYCQBIGRSLP-LKABXFAYSA-N

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-6-O-tert-butyldimethylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide
  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：

  乙酸酐 、 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester 在 吡啶 作用下， 反应 3.0h， 以2.78 g的产率得到4-methoxybenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-tert-butyldimethylsilyl-2-deoxy-3-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