(2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate] | 1252027-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate]
• 英文别名: 1-O-benzyl 2-O-tert-butyl (2R,3R,4R,5S)-3-[(2S,3R,4R,5S,6R)-3-azido-6-[(2-chloroacetyl)oxymethyl]-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)piperidine-1,2-dicarboxylate
• CAS: 1252027-38-5
• 化学式: C₅₄H₅₉ClN₄O₁₂
• 分子量: 991.535
• InChiKey: BFZHLCQJMIIALY-FXQCWLGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate] 在 hydrazinedithiocarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以72%的产率得到(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate]
  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
• 作为产物：
  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-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate 在 Me₂S₂-Tf₂O 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 以80%的产率得到(2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate]
  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.