10-undecenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactoside | 134078-52-7

• 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: 10-undecenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactoside
• 英文别名: undec-10-enyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；(2',3',6',2'',3'',4'',6''-hepta-O-acetyl)-1-undec-10-enyl-β-D-lactopyranoside；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-undec-10-enoxyoxan-2-yl]methyl acetate
• CAS: 134078-52-7
• 化学式: C₃₇H₅₆O₁₈
• 分子量: 788.841
• InChiKey: CPBVLAXHEVVSPK-ZRKHTSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  55
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  10-undecenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactoside 在 甲醇 、 sodium methylate 作用下， 反应 4.5h， 以91%的产率得到undec-10-enyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  新型的非离子单链和硼酸酯烷基糖苷表面活性剂。微波辅助糖基化和烯烃交叉复分解或“点击化学”合成：物理化学研究

  摘要：

  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。

  DOI：

  10.1016/j.tet.2010.03.115
• 作为产物：
  描述：

  10-十一烯-1-醇 、 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83.9%的产率得到10-undecenyl 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactoside
  参考文献：
  名称：

  Modified oligonucleotides and compound that can be used for synthesizing same

  摘要：

  本公开涉及生物医学技术领域，特别是涉及改良寡核苷酸和一种可用于合成相同的化合物以及一种修改寡核苷酸的方法。本公开还涉及使用改良寡核苷酸来预防和/或治疗与主体肝脏相关的疾病。

  公开号：

  US20200369703A1

文献信息

• An efficient glycosylation reaction for the synthesis of asialo GM2 analogues
  作者：Bin Sun、Aliaksei V. Pukin、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.tetlet.2006.08.008

  日期：2006.10

  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.
• 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.
• Syntheses of alkenylated carbohydrate derivatives toward the preparation of monolayers on silicon surfaces
  作者：Louis C.P.M. de Smet、Aliaksei V. Pukin、Gerrit A. Stork、C.H. Ric de Vos、Gerben M. Visser、Han Zuilhof、Ernst J.R. Sudhölter

  DOI：10.1016/j.carres.2004.09.004

  日期：2004.10

  This note describes the synthesis of different alkenylated carbohydrate derivatives suitable for direct attachment to hydrogen-terminated silicon surfaces. The derivatives were alkenylated at the C-1 position, while the remaining hydroxyl groups were protected. The development of such new carbohydrate-based sensing elements opens the access to new classes of biosensors. (C) 2004 Elsevier Ltd. All rights reserved.