undec-10-enyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 61660-73-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undec-10-enyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: undec-10-enyl-β-D-lactopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-undec-10-enoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 61660-73-9
• 化学式: C₂₃H₄₂O₁₁
• 分子量: 494.58
• InChiKey: LFZORGOUSJSBOB-QFAHURJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  undec-10-enyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-undec-10-enyloxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 IR resin (H+) 、 氢溴酸 、 sodium methylate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 undec-10-enyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient glycosylation reaction for the synthesis of asialo GM2 analogues

  摘要：

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.008

文献信息

• Novel class of non-ionic monocatenary and bolaform alkylglycoside surfactants. Synthesis by microwave-assisted glycosylation and olefin cross-metathesis or by ‘click-chemistry’: physicochemical studies
  作者：Virginie Neto、Robert Granet、Pierre Krausz

  DOI：10.1016/j.tet.2010.03.115

  日期：2010.6

  We develop herein the synthesis of a new class of monocatenary and bolaform surfactants from d-glucose, d-galactose and lactose. Two main pathways have been investigated: microwave-assisted glycosylation followed by olefin cross-metathesis, and the one-step click-chemistry methodology. Tensioactive properties of these new compounds have been studied in order to characterize the physicochemical behaviour

  我们在这里开发了从d-葡萄糖，d-半乳糖和乳糖合成一类新型的单链和硼酸盐表面活性剂。已经研究了两个主要途径：微波辅助糖基化和随后的烯烃交叉复分解，以及一步点击化学方法。为了表征这些新的基于碳水化合物的化合物在水中的物理化学行为，已对这些新化合物的张力活性特性进行了研究。
• GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis
  作者：Aliaksei V. Pukin、Carel A.G.M. Weijers、Barend van Lagen、Rainer Wechselberger、Bin Sun、Michel Gilbert、Marie-France Karwaski、Dion E.A. Florack、Bart C. Jacobs、Anne P. Tio-Gillen、Alex van Belkum、Hubert P. Endtz、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.carres.2008.01.007

  日期：2008.3

  Undee-10-enyl, undec-10-ynyl and 11-azidoundecyl glycoside analogues corresponding to the oligosaccharides of human gangliosides GM3, GM2 and GM1 were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. Due to poor water solubility of the substrates, the reactions were carried out in methanol-water media, which for the first time were shown to be compatible with the C. jejuni alpha-(2 -> 3)-sialyltransferase (CST-06) and beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CJL-30). Bioequivalence of our synthetic analogues and natural gangliosides was examined by binding to Vibrio cholerae toxin and to the B subunit of Escherichia coli heat-labile enterotoxin. This bioequivalence was confirmed by binding mouse and human monoclonal antibodies to GM1 and acute phase sera containing IgM and IgG antibodies to GM1 from patients with the immune-mediated polyneuropathy Guillain-Barre syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with C-13-H-1 correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all H-1 and C-13 chemical shifts is presented. (c) 2008 Elsevier Ltd. All rights reserved.