phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside | 1207750-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R)-5-azido-3,4-bis(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl 2-chloroacetate
• CAS: 1207750-80-8
• 化学式: C₂₈H₂₈ClN₃O₅S
• 分子量: 554.066
• InChiKey: BRZGEMLVGSMNHQ-KICATWCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside 、 tert-butyl [2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-N-(4-nitro)benzenesulfonyl-L-iditol]uronate 在 Me₂S₂-Tf₂O 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.08h， 以90%的产率得到(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-chloroacetyl-α-D-glucopyranosyl)-(1->4)-[tert-butyl [2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-N-(4-nitro)benzenesulfonyl-L-iditol]uronate]
  参考文献：
  名称：

  4-硝基苯磺酰基作为亚氨基糖的便利N保护基-乙酰肝素酶寡糖抑制剂的合成

  摘要：

  4-硝基苯磺酰基（nosyl）可有利地用于保护亚氨基糖的环氮原子。方便地引入该组，该组对大多数标准碳水化合物转化稳定，并且可以在温和条件下除去。通过合成硫酸化的寡糖（其是乙酰肝素酶的抑制剂），可以证明糖基的适用性。所述ñ - （4-硝基苯磺酰基）基团是正交与叠氮基函数。

  DOI：

  10.1016/j.tetlet.2009.11.042
• 作为产物：
  描述：

  、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of glycosaminoglycan oligosaccharides. Part 4: Synthesis of aza-l-iduronic acid-containing analogs of heparan sulfate oligosaccharides as heparanase inhibitors

  摘要：

  The synthesis of three azasugar-containing analogs of the disaccharide units of heparan sulfate, which are potential inhibitors of the enzyme heparanase, is reported. Synthetic routes were developed for the preparation of L-ido-nojirimycin type glycosyl acceptors with O-4 free. Glycosylation of these acceptors with an O-6 functionalized 2-azido-2-deoxy-n-glucose thioglycoside donor afforded the a-linked disaccharides in good yields. The advantages of using the 4-nitrobenzenesulfonyl group for the protection of the ring nitrogen of azasugars were demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.055

文献信息

• Synthesis of glycosaminoglycan oligosaccharides. Part 4: Synthesis of aza-l-iduronic acid-containing analogs of heparan sulfate oligosaccharides as heparanase inhibitors
  作者：Zsuzsánna Csíki、Péter Fügedi

  DOI：10.1016/j.tet.2010.07.055

  日期：2010.9

  The synthesis of three azasugar-containing analogs of the disaccharide units of heparan sulfate, which are potential inhibitors of the enzyme heparanase, is reported. Synthetic routes were developed for the preparation of L-ido-nojirimycin type glycosyl acceptors with O-4 free. Glycosylation of these acceptors with an O-6 functionalized 2-azido-2-deoxy-n-glucose thioglycoside donor afforded the a-linked disaccharides in good yields. The advantages of using the 4-nitrobenzenesulfonyl group for the protection of the ring nitrogen of azasugars were demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
• The 4-nitrobenzenesulfonyl group as a convenient N-protecting group for iminosugars—synthesis of oligosaccharide inhibitors of heparanase
  作者：Zsuzsánna Csíki、Péter Fügedi

  DOI：10.1016/j.tetlet.2009.11.042

  日期：2010.1

  The 4-nitrobenzenesulfonyl (nosyl) group can be used advantageously for the protection of the ring nitrogen atom of iminosugars. This group is conveniently introduced, is stable to most of the standard carbohydrate transformations and can be removed under mild conditions. The applicability of the nosyl group is demonstrated by the synthesis of sulfated oligosaccharides which are inhibitors of the enzyme

  4-硝基苯磺酰基（nosyl）可有利地用于保护亚氨基糖的环氮原子。方便地引入该组，该组对大多数标准碳水化合物转化稳定，并且可以在温和条件下除去。通过合成硫酸化的寡糖（其是乙酰肝素酶的抑制剂），可以证明糖基的适用性。所述ñ - （4-硝基苯磺酰基）基团是正交与叠氮基函数。