allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside | 147649-92-1

• 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: allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-2-(4-methoxyphenyl)-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 147649-92-1
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: NNGSKNYSTBWGNE-HDKMNVHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 在 吡啶 、 水 、 溶剂黄146 作用下， 反应 7.5h， 生成 allyl 2,3-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Structures of the glycopeptidolipid antigens of serovars 25and 26 of the Mycobacterium aviumserocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins

  摘要：

  The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. avium serovar 26 has been characterized as O-(2,4-di-O-methyl-alpha-L-fucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding D-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26-1 and 26-2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of H-1-C-13 NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the D and L enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the D-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-galactopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose.

  DOI：

  10.1016/s0008-6215(92)84233-i
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 ammonium hydroxide 、 氢溴酸 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 162.0h， 生成 allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside
  参考文献：
  名称：

  改性透明质酸二糖的化学合成

  摘要：

  本文中，我们仅使用市售的d-葡萄糖和d-葡萄糖胺盐酸盐报告了化学合成新的透明质酸低聚物的方法。合成了各种受保护的透明质酸二糖，在β- d-葡萄糖醛酸部分的C-6处带有新的官能团，以期进行结构相关的生物学活性测试。正交保护基图案允许容易地获得相应的高级低聚物。同样，对新衍生物的1 H NMR研究证明了各种官能团对分子内电子环境的影响。

  DOI：

  10.1002/chem.201701238

文献信息

• Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E
  作者：Kevin Muru、Maude Cloutier、Arianne Provost-Savard、Sabrina Di Cintio、Océane Burton、Justin Cordeil、Marie-Christine Groleau、Jean Legault、Eric Déziel、Charles Gauthier

  DOI：10.1021/acs.joc.1c01907

  日期：2021.11.5

  We describe the total synthesis of a chimeric glycolipid bearing both the partially acetylated backbone of sponge-derived agminoside E and the (R)-3-hydroxydecanoic acid chain of bacterial rhamnolipids. The branched pentaglucolipid skeleton was achieved using a [3 + 2] disconnection approach. The β-(1 → 2) and β-(1 → 4)-glycosidic bonds were synthesized through a combination of NIS/Yb(OTf)3- and TMSOTf-mediated

  我们描述了一种嵌合糖脂的全合成过程，该糖脂具有海绵衍生的 agminoside E 的部分乙酰化主链和细菌鼠李糖脂的 ( R )-3-羟基癸酸链。使用 [3 + 2] 断开方法实现了支链五糖脂骨架。β-(1 → 2) 和 β-(1 → 4)-糖苷键是通过结合 NIS/Yb(OTf) 3 - 和 TMSOTf 介导的硫代甲苯基立体选择性糖基化，N-苯基三氟乙酰亚胺酯和三氯乙酰亚胺酯供体。后期五乙酰化，（2-叠氮甲基）苯甲酰基的施陶丁格还原，然后连续流动微流体氢解完成了结构简化的糖脂的全合成，其聚糖部分的部分乙酰化模式与agminoside E相同。我们的研究为海绵来源的agminosides的全合成和了解它们在海绵中的生物学功能奠定了基础。
• Ganglioside GQ1b: Efficient Total Synthesis and the Expansion to Synthetic Derivatives To Elucidate Its Biological Roles
  作者：Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1021/jo8027888

  日期：2009.4.17

  The convergent total synthesis of ganglioside GQ1b based on the “cassette approach” between the nonreducing end GQ1b-core heptasaccharide and glucosylceramide building blocks was accomplished in high overall yield. The use of a sialylα(2→8)sialylα(2→3)galactose sequence as the key building block enhanced the efficiency of the glycan assembly and led to preparative-scale synthesis readily applicable

  基于“盒式方法”，在非还原性末端GQ1b核心七糖和葡萄糖基神经酰胺结构单元之间实现了神经节苷脂GQ1b的聚合全合成，从而获得了较高的总收率。使用唾液酸基α（2→8）唾液酸基α（2→3）半乳糖序列作为关键构建基块提高了聚糖组装体的效率，并导致易于用于大规模制备的制备规模合成。另外，p的明智选择葡糖神经酰胺上的-甲氧基苄基保护基为先前的合成问题提供了解决方案，包括降低脱保护步骤的收率，并导致总收率的提高。此外，为了阐明其生物学作用，利用相似的方法系统地合成了高产率的非天然GQ1b衍生物。
• A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded
  作者：Ralf Kosmol、Lothar Hennig、Peter Welzel、Matthias Findesien、Dietrich Müller、Astrid Markus、Jean van Heijenoort

  DOI：10.1002/prac.19973390162

  日期：——

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.
• Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
  作者：Marco Mende、Martin Nieger、Stefan Bräse

  DOI：10.1002/chem.201701238

  日期：2017.9.7

  report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d‐glucose and d‐glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C‐6 of the β‐d‐glucuronic acid moiety with a view to structure‐related biological activity tests. The orthogonal protecting group pattern allows ready

  本文中，我们仅使用市售的d-葡萄糖和d-葡萄糖胺盐酸盐报告了化学合成新的透明质酸低聚物的方法。合成了各种受保护的透明质酸二糖，在β- d-葡萄糖醛酸部分的C-6处带有新的官能团，以期进行结构相关的生物学活性测试。正交保护基图案允许容易地获得相应的高级低聚物。同样，对新衍生物的1 H NMR研究证明了各种官能团对分子内电子环境的影响。
• Structures of the glycopeptidolipid antigens of serovars 25and 26 of the Mycobacterium aviumserocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins
  作者：Gerald O Aspinall、David W Gammon、Ramesh K Sood、Delphi Chatterjee、Becky Rivoire、Patrick J Brennan

  DOI：10.1016/s0008-6215(92)84233-i

  日期：1992.12

  The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. avium serovar 26 has been characterized as O-(2,4-di-O-methyl-alpha-L-fucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding D-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26-1 and 26-2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of H-1-C-13 NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the D and L enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the D-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-galactopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose.