4-nitrophenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl (1-> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucolyranoside | 249552-16-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-nitrophenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl (1-> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucolyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-5-benzoyloxy-6-[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(4-nitrophenyl)sulfanyloxan-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl benzoate
• CAS: 249552-16-7
• 化学式: C₅₃H₄₅NO₁₇S
• 分子量: 1000.0
• InChiKey: KYVAFCMDLSLRIG-KMKQRQEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  72
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  271
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl (1-> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucolyranoside 、 4-acetamidophenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1-> 4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1-> 3)]-2-phthalimido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以71%的产率得到4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1-> 3)]-(2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranosyl)-(1-> 3)-2,6-di-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2,3,6...
  参考文献：
  名称：

  Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses

  摘要：

  Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00080-4
• 作为产物：
  描述：

  4-nitrophenyl 3',4'-O-isopropylidene-1-thio-β-D-lactopyranoside 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-nitrophenyl 2,6-di-O-benzoyl-β-D-galactopyranosyl (1-> 4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucolyranoside
  参考文献：
  名称：

  Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses

  摘要：

  Glycosylation of 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-beta-D-glucopyranoside with phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside in the presence of NIS and TfOH as catalyst gave the lactosamine derivative regiospecifically in high yield. Further 3-O-fucosylation with phenyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside using DMTST as promoter afforded the Le(x) trisaccharide intermediate. The latent glycosyl donor was transformed into its active form (p-acetamidothiophenyl) by reduction with zinc in acetic acid and N-acetylation. Glycosidation with p-nitrothiophenyl lactoside acceptor in the presence of NIS/TfOH as catalyst gave the Le(x) pentasaccharide in 71% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00080-4