6-(benzyloxycarbonylamino)hexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 85472-19-1

• 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: 6-(benzyloxycarbonylamino)hexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: 6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-4,6-O-benzylidene-2-deoxy)-β-D-glucopyranoside；6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-4,6-di-O-benzylidene-2-deoxy-β-D-glucopyranoside；benzyl N-[6-[[(2R,4aR,6R,7R,8R,8aS)-7-acetamido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]hexyl]carbamate
• CAS: 85472-19-1
• 化学式: C₂₉H₃₈N₂O₈
• 分子量: 542.629
• InChiKey: OITVFVAQFLYCKX-BXZOIBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(benzyloxycarbonylamino)hexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 palladium(II) oxide 氢气 、 sodium hydride 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 溶剂黄146 为溶剂， 反应 78.0h， 生成 (6-aminohexyl) β-glycoside of N-acetylmuramyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  N-乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺的ω-氨基烷基β-糖苷及其与脑膜炎球菌C组多糖的缀合物

  摘要：

  由2-甲基-（3,4,6-三-O-乙酰基）合成N-乙酰基muramyl-L-丙氨酰-D-异谷氨酰胺的6-氨基己基β-糖苷及其间隔臂连接的类似物（3.8 nm） -1,2-二脱氧-α-D-吡喃葡萄糖基）-[2,1-d] -2-恶唑啉，并与脑膜炎球菌C组多糖偶联，试图增强多糖抗原的免疫原性。

  DOI：

  10.1016/0008-6215(83)88218-4
• 作为产物：
  描述：

  6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-(benzyloxycarbonylamino)hexyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4

文献信息

• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of Sulfated Lex-Trisaccharides
  作者：W. Stahl、U. Sprengard、G. Kretzschmar、D. W. Schmidt、H. Kunz

  DOI：10.1002/prac.19953370196

  日期：——

  The regioselective sulfation of a Le(x)-trisaccharide having free hydroxyl groups in 2-, 3- and 4- position of the galactose elucidated their different reactivities and gave mono- and disulfated Le(x) derivatives.
• Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides
  作者：Anne-Marie M. van Roon、Begoña Aguilera、Francisco Cuenca、Alexandra van Remoortere、Gijsbert A. van der Marel、André M. Deelder、Herman S. Overkleeft、Cornelis H. Hokke

  DOI：10.1016/j.bmc.2005.02.009

  日期：2005.5

  Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million people in the tropics. The fucosylated structures are thought to play an important role in the immunology of schistosomiasis. Defined schistosomal oligosaccharides that enable immunological studies are difficult to obtain from natural sources. Therefore, we have chemically synthesized spacer-linked GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, Fuc alpha 1-2Fuc alpha 1-3GlcNAc, and Fuc alpha 1-2Fuc alpha 1-2Fuc alpha 1-3GlcNAc. This series of linear oligosaccharides was used to screen a library of anti-schistosome monoclonal antibodies by surface plasmon resonance spectroscopy. Interestingly, the reactive antibodies could be grouped according to their specificity for the different oligosaccharides tested, showing that these oligosaccharides form different immunological entities based on the number and linkage of the fucose residues. Subsequently, the thus defined monoclonal antibodies were used to visualize the expression of the corresponding oligosaccharide epitopes by adult Schistosoma mansoni worms. (c) 2005 Elsevier Ltd. All rights reserved.
• ω-Aminoalkyl β-glycosides of N-acetylmuramyl-l-alanyl-d-isoglutamine, and their conjugates with meningococcal group C polysaccharide
  作者：Mitree M. Ponpipom、Kathleen M. Rupprecht

  DOI：10.1016/0008-6215(83)88218-4

  日期：1983.2

  The 6-aminohexyl beta-glycoside of N-acetylmuramyl-L-alanyl-D-isoglutamine and its spacer-arm-linked analog (3.8 nm) were synthesized from 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2- oxazoline, and coupled with meningococcal group C polysaccharide in attempts to enhance the immunogenicity of the polysaccharide antigen.

  由2-甲基-（3,4,6-三-O-乙酰基）合成N-乙酰基muramyl-L-丙氨酰-D-异谷氨酰胺的6-氨基己基β-糖苷及其间隔臂连接的类似物（3.8 nm） -1,2-二脱氧-α-D-吡喃葡萄糖基）-[2,1-d] -2-恶唑啉，并与脑膜炎球菌C组多糖偶联，试图增强多糖抗原的免疫原性。