4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 212128-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-d-glucopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-(4-nitrophenyl)sulfanyloxan-2-yl]methyl acetate
• CAS: 212128-05-7
• 化学式: C₂₆H₂₄N₂O₁₁S
• 分子量: 572.549
• InChiKey: WOYMIVURHONWSV-HDXRJONQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  197
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.92h， 生成 4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-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
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  离子淌度-质谱分析辅助的一锅法糖基化策略合成 N-连接寡糖

  摘要：

  N-聚糖是几种细胞糖蛋白的主要成分。N-聚糖合成的一锅法对于快速生成纯样品以确定其生物学功能至关重要。在此，我们描述了一种通过 IM-MS 分析方法辅助合成N-聚糖的双一锅策略，用于快速筛选优化的糖基化反应条件。这项研究包括三氟甲磺酸酯介导的直接 β-甘露糖基化和串联糖基化，采用一锅法合成具有挑战性的N-连接三糖核心β-5。此外， N-连接三糖核心的一锅顺序糖基化7提供多种高甘露糖型N-聚糖，具有出色的立体选择性和区域选择性。特别是，应用离子淌度-质谱定量分析来确定粗反应混合物的立体选择性和区域选择性结果，以开发高效的一锅法。

  DOI：

  10.1021/acs.joc.2c00184

文献信息

• Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4
  作者：Suoding Cao、Fernando Hernández-Matéo、René Roy

  DOI：10.1080/07328309808002341

  日期：1998.5.1

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.