2,4,6-tri-O-acetyl-3-O-benzyl-D-glucopyranose | 119870-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tri-O-acetyl-3-O-benzyl-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-hydroxy-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 119870-24-5
• 化学式: C₁₉H₂₄O₉
• 分子量: 396.394
• InChiKey: RRZIXYBVYHEMNH-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(benzyl)-benzyloxycarbonyl-5-aminopentyl 2-azido-3-O-benzyl-2-deoxy-6-O-tert-butyl-diphenylsilyl-α-D-glucopyranoside 、 2,4,6-tri-O-acetyl-3-O-benzyl-D-glucopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以80%的产率得到N-(benzyl)-benzyloxycarbonyl-5-aminopentyl O-(2-O-acetyl-4-O-acetyl-6-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-(1→4)-O-2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Unique Heparin Mimetic Hexasaccharide for Structure–Activity Relationship Studies

  摘要：

  To date, the structure-activity relationship studies of heparin/heparan sulfate with their diverse binding partners such as growth factors, cytokines, chemokines, and extracellular matrix proteins have been limited yet provide early insight that specific sequences contribute to this manifold biological role. This has led to an impetus for the chemical synthesis of oligosaccharide fragments of these complex polysaccharides, which can provide an effective tool for this goal. The synthesis of three heparin mimetic hexasaccharides with distinct structural patterns is described herein, and the influence of the targeted substitution on their bioactivity profiles is studied using in vitro affinity and/or inhibition toward different growth factors and proteins. Additionally, the particularly challenging synthesis of an irregular hexasaccharide is reported, which, interestingly, in spite of being considerably structurally similar with its two counterparts, displayed a unique and remarkably distinct profile in the test assays.

  DOI：

  10.1021/jm4016069
• 作为产物：
  描述：

  1,2,4,6-四-o-乙酰基-3-o-苄基-beta-d-吡喃葡萄糖 生成 2,4,6-tri-O-acetyl-3-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  AUGE, CLAUDINE;DAVID, SERGE;GAUTHERON, CHRISTINE;MALLERON, ANNIE;CAVAYE, +, NEW J. CHEM., 12,(1988) N 8-9, C. 733-744

  摘要：

  DOI：

文献信息

• Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei
  作者：Simon Krauter、Christina Schäffer、Paul Kosma

  DOI：10.24820/ark.5550190.p011.358

  日期：——

  A disaccharide implicated in anchoring of bacterial Surface-layer proteins to secondary cell wall glycopolymers has been prepared by glycosylation of a protected N-acetyl glucosamine acceptor with a glucopyranosyl donor to generate the β-(14)-linkage. Subsequent inversion of the configuration and azide introduction at position 2 with triflic anhydride, however, led to formation of a tetrazole derivative

  通过将受保护的 N-乙酰氨基葡萄糖受体与吡喃葡萄糖基供体进行糖基化以产生 β-(1→4)-键，已经制备了一种与细菌表面层蛋白锚定到次生细胞壁糖聚合物有关的二糖。然而，随后用三氟甲磺酸酐反转构型和在 2 位引入叠氮化物，导致形成四唑衍生物。或者，通过叠氮化钠、还原和 N-乙酰化置换 2O-甲磺酸盐能够转化为远端 N-乙酰基-β-甘露糖胺残基。后一个单元的丙酮酸化和全局脱保护提供了来自类芽孢杆菌的双糖重复单元作为晶体学和结合研究的配体。