4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside | 249552-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4,5-dihydroxy-2-(4-nitrophenyl)sulfanyloxan-3-yl]isoindole-1,3-dione
• CAS: 249552-05-4
• 化学式: C₃₆H₃₆N₂O₈SSi
• 分子量: 684.842
• InChiKey: FZLQNYQNQTYIQM-NRLOGRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  167
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 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 2.92h， 生成 4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-3-O-acetyl-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
  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 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
  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

文献信息

• Active–latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses
  作者：Suoding Cao、Zhonghong Gan、René Roy

  DOI：10.1016/s0008-6215(99)00080-4

  日期：1999.5

  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.