2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-L-iditol | 1252027-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-L-iditol
• CAS: 1252027-18-1
• 化学式: C₃₉H₃₉NO₆
• 分子量: 617.742
• InChiKey: USUKNGXYUFOQFT-CDBYGCFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

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 、 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-L-iditol 在 N,N-二甲基氨基-N-甲苯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.5h， 以59%的产率得到(2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-L-iditol]
  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：

  2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-imino-4,6-O-(1-naphthyl)methylene-L-iditol 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以67%的产率得到2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-6-O-(1-naphthyl)methyl-L-iditol
  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