2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl trichloroacetimidate | 245110-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranosyl trichloroacetimidate
• CAS: 245110-00-3
• 化学式: C₂₂H₂₁Cl₃N₄O₅
• 分子量: 527.792
• InChiKey: DKCFPXUOXFLHPU-PJBUMPDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118.76
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 在 重铬酸吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 乙酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 21.5h， 生成 allyl (2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl-2-O-acetyl-3-O-benzyl-α-L-idopyranosiduronate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8
• 作为产物：
  描述：

  dimethylthexylsilyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside 在 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of disaccharidic sub-units of a new series of heparin related oligosaccharides

  摘要：

  The chemical synthesis of disaccharides 1 and 2, useful building-blocks for the preparation of a new series of heparin related oligosaccharides containing the unusual sequence (GlcN-IdoA)(n), is described. In addition, the orthogonality of the protective groups would allow access to a wide array of differently sulfated oligosaccharides. As the simplest members of this new class of oligomer, the synthesis of sulfated disaccharides 3 and 4 fully deprotected is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00526-8

文献信息

• Synthesis of a Potential 10E4 Tetrasaccharide Antigen Involved in Scrapie Pathogenesis
  作者：Pascal Bindschädler、Christian Noti、Eva Castagnetti、Peter H. Seeberger

  DOI：10.1002/hlca.200690234

  日期：2006.11

  To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2 + 2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biological role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using

  为了检验四糖3参与瘙痒病发病机理的假说，合成了在还原端用胺连接基官能化的四糖衍生物32。选择（2 + 2）糖基化方法以完全保护的形式提供目标化合物。为了研究其生物学作用，使用Traut试剂将四糖32进一步官能化为相应的硫醇33。在合成过程中，N，N-二乙酰基保护基被证明对自由基和酸性条件不稳定。
• 10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c
  作者：Martin-Lomas, Manuel、Flores-Mosquera, Maria、Chiara, Jose Luis

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c

  日期：——
• Glycosylation with Trichloroacetimidates in Ionic Liquids:  Influence of the Reaction Medium on the Stereochemical Outcome
  作者：Anna Rencurosi、Luigi Lay、Giovanni Russo、Enrico Caneva、Laura Poletti

  DOI：10.1021/jo050704x

  日期：2005.9.1

  [GRAPHICS]The glycosylation with trichloroacetimidates derived from different glycopyranoses bearing a nonparticipating group at C-2 was explored in different ionic liquids as solvents. The stereoselectivity of the reaction was significantly affected by the reaction media and by the anomeric configuration of the donor.