benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside | 57783-80-9

• 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: benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
• 英文别名: benzyl 4,6-O-benzylidene-2,3-di-O-benzyl-β-D-galactopyranoside；1,2,3-Tri-O-benzyl-4,6-O-benzylidene-b-D-galactopyranose；(4aR,6R,7R,8S,8aS)-2-phenyl-6,7,8-tris(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 57783-80-9
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: GQMVOFUMWKGWCK-JYYQWNAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以91%的产率得到苄基6-O-苯甲酰基-2,3-二-O-苄基吡喃己糖苷
  参考文献：
  名称：

  鼠李糖半乳糖醛酸I的β-1,4-连接半乳聚糖侧链的合成

  摘要：

  直链的和合成（1→6） -支化的β-（1→4） - d -galactans，鼠李我描述了果胶多糖的侧链。该策略依赖于正戊烯基二糖的迭代偶联，随后是常见六糖核心的晚期糖基化。与共价接头反应并固定在N-羟基琥珀酰亚胺（NHS）修饰的玻璃表面上可以生成碳水化合物微阵列。聚糖阵列能够以高通量的方式研究蛋白质与碳水化合物的相互作用，本文通过mAb和CBM的结合研究证明了这一点。

  DOI：

  10.1002/chem.201602197
• 作为产物：
  描述：

  苄基Beta-D-吡喃半乳糖苷 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

  摘要：

  三半乳糖醛酸单甲酯1-3的合成被描述为向果胶低聚糖迈进的一般策略的一部分。所需的单体构建单元均从葡萄糖五乙酸酯大规模制备。糖基化反应是在葡萄糖糖基供体和受体之间使用n-戊烯糖基化技术进行的。所需的α-异头物的产率在50%到74%之间。由此获得的三半乳糖通过C-6位氧化。根据该位置的保护基团，氧化或者产生羧酸或相应的甲酯。因此，可以制备具有区域选择性引入甲酯的半乳糖醛酸低聚物。

  DOI：

  10.1039/b006981g

文献信息

• Characterization of the LM5 pectic galactan epitope with synthetic analogues of β-1,4-d-galactotetraose
  作者：Mathias C.F. Andersen、Irene Boos、Susan E. Marcus、Stjepan K. Kračun、Maja Gro Rydahl、William G.T. Willats、J. Paul Knox、Mads H. Clausen

  DOI：10.1016/j.carres.2016.10.012

  日期：2016.12

  Plant cell wall glycans are important polymers that are crucial to plant development and serve as an important source of sustainable biomass. The study of polysaccharides in the plant cell wall relies heavily on monoclonal antibodies (mAbs) for localization and visualization of glycans, using e.g. immunofluorescent microscopy. Here, we describe the detailed epitope mapping of the mAb LM5 that is shown

  植物细胞壁聚糖是重要的聚合物，对植物的生长至关重要，并且是可持续生物量的重要来源。植物细胞壁中多糖的研究在很大程度上依赖于单克隆抗体（mAb），例如使用免疫荧光显微镜对聚糖进行定位和可视化。在这里，我们描述了mAb LM5的详细表位作图，显示其可与线性β-1,4-连接的半乳​​聚糖的非还原端的最少三个糖残基结合。该研究将半乳聚糖的从头合成类似物与碳水化合物微阵列和竞争性抑制ELISA结合使用，以分析抗体与碳水化合物的相互作用。
• Anchimeric assistance by the anomeric phenylthio group in the nucleophilic substitution of a 6-O-trifluoromethanesulfonyl-β-d-galactopyranoside
  作者：Muriel Compain-Batissou、Lamya Mesrari、Daniel Anker、Alain Doutheau

  DOI：10.1016/s0008-6215(99)00048-8

  日期：1999.3

  Abstract Nucleophilic displacement by the cyanide anion of the 6- O -triflyl group in phenyl 6- O -triflyl-2,3-di- O -benzyl-4- O - p -methoxybenzyl-1-thio-β- d -galactopyranoside takes place via an intermediate 1,6-sulfonium salt resulting from the anchimeric assistance of the C-1 phenylthio group.

  摘要苯基6-O-triflyl-2,3-di-O-苄基-4-O-对甲氧基苄基-1-硫代-β-d-吡喃半乳糖苷中6-O-triflyl基团的氰化物阴离子可亲核取代通过由C-1苯硫基的邻氨基苯甲酸辅助产生的中间体1，6-s盐发生。
• Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors
  作者：Yoshiyuki Kobayashi、Masao Shiozaki、Osamu Ando

  DOI：10.1021/jo00113a041

  日期：1995.4

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.
• Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ_1b⁺.
  作者：Yukishige Ito、Shigeki Nunomura、Shohei Shibayama、Tomoya Ogawa

  DOI：10.1021/jo00032a601

  日期：1992.3

  The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i.e., 1 (alpha-NeuAc2 -->-8-alpha-NeuAc2 --> 3-beta-Gal1 --> 4Glc), 2 (alpha-NeuAc2 --> 8-alpha-NeuAc2 --> 3Gal), 3 (GalNAc), 4 (alpha-NeuAc2 --> 8NeuAc), 5 (beta-Gal1 -->- 3GalNAc), and 42 [beta-Gal1 --> 3-beta-GalNAc1 --> 4(alpha-NeuAc2 --> 3)beta-Gal --> 4Glc], is described. All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments. The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary. Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration. Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed. The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAc-beta-1 --> 4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.
• A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid
  作者：Mads H. Clausen、Malene R. Jørgensen、Jesper Thorsen、Robert Madsen

  DOI：10.1039/b006981g

  日期：——

  The synthesis of monomethyl-esterified trigalacturonans 1–3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired α-anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.

  三半乳糖醛酸单甲酯1-3的合成被描述为向果胶低聚糖迈进的一般策略的一部分。所需的单体构建单元均从葡萄糖五乙酸酯大规模制备。糖基化反应是在葡萄糖糖基供体和受体之间使用n-戊烯糖基化技术进行的。所需的α-异头物的产率在50%到74%之间。由此获得的三半乳糖通过C-6位氧化。根据该位置的保护基团，氧化或者产生羧酸或相应的甲酯。因此，可以制备具有区域选择性引入甲酯的半乳糖醛酸低聚物。