benzyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranose | 116525-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranose
• 英文别名: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside；benzyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Glc(b)-O-Bn；(2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(phenylmethoxy)-6-[[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxane
• CAS: 116525-10-1
• 化学式: C₆₈H₇₀O₁₁
• 分子量: 1063.3
• InChiKey: VFMOICMXCOZMPY-WUTAXNSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  79
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 benzyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties

  摘要：

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.

  DOI：

  10.1021/jacs.8b11882

文献信息

• Dehydrative Glycosylation with the Hendrickson Reagent
  作者：Matteo Mossotti、Luigi Panza

  DOI：10.1021/jo2015856

  日期：2011.11.4

  The Hendrickson reagent is able to perform efficiently dehydrative glycosylation of 1-hydroxyglycosyl donors. The reaction occurs under mild conditions through an anomeric oxophosphonium intermediate detected by nuclear magnetic resonance. Further insight into the mechanism was gained by 18O labeling of anomeric OH.

  亨德里克森试剂能够有效地进行1-羟基糖基供体的脱水糖基化。该反应在温和条件下通过核磁共振检测到的异头氧代intermediate中间体而发生。通过18 O标记异头OH获得了对该机理的进一步了解。
• Dehydrative Glycosylation by Diethylaminosulfur Trifluoride (DAST)–Tin(II) Trifluoromethanesulfonate–Tetrabutylammonium Perchlorate–Triethylamine System
  作者：Motoko Hirooka、Shinkiti Koto

  DOI：10.1246/bcsj.71.2893

  日期：1998.12

  Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose and O-α-D-glu

  通过使用由二乙氨基三氟化硫 (DAST)、三氟甲磺酸锡 (II)、四丁基高氯酸铵和三乙胺组成的缩合试剂系统，使用 2,3,4,6-四-O-苄基-D-吡喃葡萄糖进行脱水糖基化. 使用该系统，两种四糖，O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-D -吡喃葡萄糖和 O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→4)-D-吡喃葡萄糖合成的。
• Synthesis of 6-O-α-d-glucopyranosylcyclomaltoheptaose
  作者：Péter Fügedi、Pál Nánási、József Szejtli

  DOI：10.1016/0008-6215(88)84140-5

  日期：1988.5

  Abstract (2,3-Di- O -acetyl)hexakis(2,3,6-tri- O -acetyl)cyclomaltoheptaose was prepared by reaction of cyclomaltoheptaose with tert -butyldimethylsilyl chloride in pyridine followed by acetylation and desilylation. Glycosylation with 2,3,4,6-tetra- O -benzyl-1- O -trichloroacetimidoyl-α- d -glucopyranose, using trifluoromethanesulfonic acid as catalyst, and removal of the protecting groups from the

  摘要通过将环麦芽庚糖与叔丁基二甲基甲硅烷基氯在吡啶中反应，然后进行乙酰化和去甲硅烷基化反应，制得（2,3-二-O-乙酰基）六（2,3,6-三-O-乙酰基）环麦芽九糖。使用三氟甲磺酸作为催化剂，用2,3,4,6-四-O-苄基-1-O-三氯乙酰亚胺基-α-d-吡喃葡萄糖进行糖基化，然后从产物中除去保护基，得到标题化合物。
• FUGEDI, PETER;NANASI, PAL;SZEJTLI, JOZSEF, CARBOHYDR. RES., 175,(1988) N 2, 173-181
  作者：FUGEDI, PETER、NANASI, PAL、SZEJTLI, JOZSEF

  DOI：——

  日期：——