6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside | 62205-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside
• 英文别名: 6-[(N-Benzyloxycarbonyl)amino]hexyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside；6-[N-(benzyloxycarbonylamino)hexyl]-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside；6-(benzyloxycarbonylamino)-1-hexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside；N-benzyloxycarbonyl-6-aminohexyl-N-acetyl-2-amino-2-deoxy-3,4,6-tri-O-acetyl-β-D-gluco-pyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[6-(phenylmethoxycarbonylamino)hexoxy]oxan-2-yl]methyl acetate
• CAS: 62205-56-5
• 化学式: C₂₈H₄₀N₂O₁₁
• 分子量: 580.632
• InChiKey: MAFNZJXDZCVRTB-RFNQJFSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以50%的产率得到6-[(N-Benzyloxycarbonyl)amino]hexyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  含乳糖胺和唾液酸化的路易斯x单元侧链的糖聚合物和顺序糖肽的化学酶法合成

  摘要：

  已经以化学酶促的方式合成了各种带有N-乙酰基乳糖胺或唾液酸化的Lewis x单元的糖缀合物。这包括与丙烯酰胺共聚的糖聚合物的合成，其糖胺单元被不同种类的侧链取代。还已经制备并聚合了具有不同间隔臂葡糖胺单元的糖肽。然后使用糖基转移酶拉长糖链，以提供新的连续糖肽。在这些情况下，聚合糖簇效应导致高效的酶促糖基化。然而，根据用于每种底物的反应条件，已经注意到一些差异。

  DOI：

  10.1039/b001612h
• 作为产物：
  描述：

  氯甲酸苄酯 在 三乙胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 6-(N-benzyloxycarbonylamino)hexyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] TRIPTOLIDE CONJUGATES AND USES THEREOF
  [FR] CONJUGÉS DE TRIPTOLIDE ET LEURS UTILISATIONS

  摘要：

  本公开提供了三鞭酸酯化物，制备这种化合物的方法，包含这种化合物的药物组合物和药品，以及使用这种化合物治疗癌症、免疫调节和/或炎症等疾病/病症的方法。

  公开号：

  WO2022040487A1

文献信息

• Synthesis of 6-amino-1-hexyl 2-acetamido-2-deoxy-3-, -4-, and -6-O-β-D-galactopyranosyl-β-D-glucopyranosides
  作者：John Vernon、Saul Roseman、Chuan Lee Yuan

  DOI：10.1016/s0008-6215(00)85520-2

  日期：1980.6

  Abstract 6-Aminohexyl glycosides of β- D -Gal→β- D -GlcNAc disaccharides having β-(1→3)-, β-(1→4)-, and β-(1→6)-Iinkages were prepared. 6-(Benzyloxycarbonylamino)-1-hexanol was glycosylated with 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-α- D -glucopyranosyl chloride, to yield (80 %) a crystalline β-glycoside acetate (3), Deacetylation of 3 , followed by isopropylidenation (2,2-dimethoxypropane-TsOH)

  摘要制备了具有β-（1→3）-，β-（1→4）-和β-（1→6）-构图的β-D-Gal→β-D-GlcNAc二糖的6-氨基己基糖苷。用2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯将6-（苯甲氧基羰基氨基）-1-己醇糖基化，得到（80％）结晶β-糖苷乙酸（3），3的脱乙酰基，然后异丙基化（2，2-二甲氧基丙烷-TsOH），以总收率84％得到结晶的4，6-O-异亚丙基衍生物（5）。5 [苄基溴-BaO-Ba（OH 2）在N，N-二甲基甲酰胺中的苯甲酰化]生成其3-O-苄基衍生物，将其转化为6-（苄氧基羰基氨基）-1-己基2-乙酰氨基-3- O-苄基-2-脱氧-β-D-吡喃葡萄糖苷（7），总产率为69％。7、2、3、4的糖基化，6-四-O-乙酰基-α-D-吡喃半乳糖基溴化物（12）和三氟甲磺酸银在干燥的CH 2 Cl 2中在0°产生β-（1→6）-二糖苷（17），产
• Synthesis of 2-deoxy-hexopyranosyl derivatives of uridine as donor substrate analogues for glycosyltransferases
  作者：Ilona Wandzik、Tadeusz Bieg、Marianna Czaplicka

  DOI：10.1016/j.bioorg.2009.08.001

  日期：2009.12

  A series of 2-deoxy-hexopyranosyl derivatives of uridine have been synthesized as analogues of UDP-sugar. These compounds were tested as inhibitors against bovine β-1,4-galactosyltransferase I in fluorescent assays and showed no significant inhibition.

  已经合成了一系列尿苷的2-脱氧-己吡喃糖基衍生物，作为UDP-糖的类似物。这些化合物在荧光测定法中作为牛β-1,4-半乳糖基转移酶I的抑制剂进行了测试，未显示出明显的抑制作用。
• 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 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.
• Cellular uptake of N-acetyl-d-galactosamine-, N-acetyl-d-glucosamine- and d-mannose-containing fluorescent glycoconjugates investigated by liver intravital microscopy
  作者：Svetlana Yu. Maklakova、Victor A. Naumenko、Andrey D. Chuprov、Maria P. Mazhuga、Nikolai V. Zyk、Elena K. Beloglazkina、Alexander G. Majouga

  DOI：10.1016/j.carres.2020.107928

  日期：2020.3