isopropyl 3,4-di-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 493019-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 3,4-di-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-4-acetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(1,3-dioxoisoindol-2-yl)-6-propan-2-ylsulfanyloxan-3-yl] acetate
• CAS: 493019-30-0
• 化学式: C₂₇H₃₉NO₈SSi
• 分子量: 565.76
• InChiKey: BXTXBEFWHRMGHV-HDXRJONQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  isopropyl 3,4-di-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 octyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (1→6)-β-d-glucosamine hexasaccharide, a potential antitumor and immunostimulating agent

  摘要：

  (1→6)-β-D-氨基葡萄糖六糖链通过使用异丙基硫糖苷作为所有偶联步骤中的糖基供体，采用汇聚式合成方法成功制备。目标化合物在小鼠S-180肿瘤模型研究中显示出良好的抗肿瘤活性。(C) 2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(02)01812-9
• 作为产物：
  描述：

  2-deoxy-2-phthalimido-D-glucopyranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 isopropyl 3,4-di-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (1→6)-β-d-glucosamine hexasaccharide, a potential antitumor and immunostimulating agent

  摘要：

  (1→6)-β-D-氨基葡萄糖六糖链通过使用异丙基硫糖苷作为所有偶联步骤中的糖基供体，采用汇聚式合成方法成功制备。目标化合物在小鼠S-180肿瘤模型研究中显示出良好的抗肿瘤活性。(C) 2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0040-4039(02)01812-9

文献信息

• A practical synthesis of a (1→6)-linked β-d-glucosamine nonasaccharide
  作者：Feng Yang、Yuguo Du

  DOI：10.1016/s0008-6215(02)00494-9

  日期：2003.3

  A (1 --> 6)-beta-D-glucosamine nonasaccharide was convergently synthesized using isopropyl thioglycosides as donors. Anomeric acetylated glucosamine derivatives were proved to be good acceptors in the NIS/TMSOTf catalyzed glycosylation. The target nonasaccharide showed a mild antitumor activity against H-22 on the preliminary mice tests. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of a C3-symmetric (1→6)-N-acetyl-β-d-glucosamine octadecasaccharide using click chemistry
  作者：Qi Chen、Feng Yang、Yuguo Du

  DOI：10.1016/j.carres.2005.08.013

  日期：2005.11

  A C-3-symmetric (1-->6)-N-acetyl-beta-D-glucosamine octadecasaccharide was convergently synthesized on the basis of a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of azide and alkyne. The target octadecasaccharide showed good antitumor activity against H22 in the preliminary mice tests. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of biantennary β-d-(1→6) glucosamine oligosaccharides
  作者：Feng Yang、Yuxia Hua、Yuguo Du

  DOI：10.1016/s0008-6215(03)00170-8

  日期：2003.6

  Biantermary beta-D-(1 --> 6) glucosamine hexa-, octa-, and dodecaoligosaccharide derivatives were synthesized convergently using isopropyl thioglycosides as donors in NIS/TMSOTf-catalyzed glycosylation. (C) 2003 Elsevier Science Ltd. All rights reserved.