2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside | 123956-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 123956-78-5
• 化学式: C₁₄H₂₈O₆Si
• 分子量: 320.458
• InChiKey: IZEHFDXZFJUDAT-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3,4-O-Isopropyliden-D-galactopyranose
  参考文献：
  名称：

  Expedient synthesis of a series of N-acetyllactosamines

  摘要：

  A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00485-0
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 、 2,2-二甲氧基丙烷 在 硫酸 、 N,N-二甲基甲酰胺 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以70%的产率得到2-(trimethylsilyl)ethyl 3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  磷酸化半乳糖衍生物的合成及类胰岛素活性

  摘要：

  已进行了分离为钠盐的多磷酸化半乳糖苷6、8、10、13、16和20的合成。分别通过2-（三甲基甲硅烷基）乙基半乳糖苷3和2的糖基化以及随后的完全脱保护来制备非磷酸化的二糖17和三糖21。磷酸化衍生物的初步胰岛素样活性已有报道。

  DOI：

  10.1016/0008-6215(93)84177-8

文献信息

• Synthesis of a d,d- and l,d-heptose-containing hexasaccharide corresponding to a structure from Haemophilus ducreyi lipopolysaccharides
  作者：Christian Bernlind、Simon Bennett、Stefan Oscarson

  DOI：10.1016/s0957-4166(99)00554-6

  日期：2000.2

  The synthesis of a linear hexasaccharide, 2-(4-trifluoroacetamidophenyl)ethyl (β-d-galactopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-(β-d-galactopyranosyl)-(1→4)-(d-glycero-α-d-manno-heptopyranosyl)-(1→6)-(β-d-glucopyranosyl)-(1→4)-l-glycero-α-d-manno-heptopyranoside, corresponding to a structure found in Haemophilus ducreyi LPS, is described. A Barbier reaction between benzyloxymethyl

  线性六糖2-（4-三氟乙酰氨基苯基）乙基（β-d-吡喃半乳糖基）-（1→4）-（2-乙酰胺基-2-脱氧-β-d-吡喃葡萄糖基）-（1→3）的合成-（β-d-吡喃半乳糖基）-（1→4）-（d-甘油-α-d-甘露聚糖-庚基吡喃糖基）-（1→6）-（β-d-吡喃葡萄糖基）-（1→4）-l描述了对应于在杜克氏嗜血杆菌LPS中发现的结构的-甘油-α-d-甘露聚糖-七吡喃糖苷。苄氧基甲基氯与适当保护的6-aldo-1-thio-mannopyranoside之间的Barbier反应产生了d，d-和l，d-庚吡喃糖苷（2和3，比率2：3），将其分离并同时使用在综合中。p-甲氧基苄基和氯乙酰基用作临时保护基团，在存在持久性苄基，乙酰基，苯甲酰基和异亚丙基的情况下分别通过用DDQ / H 2 O和肼二硫代碳酸酯处理选择性地除去。始终使用NIS / TfOH或DMTST作为促进剂，将硫糖苷用作供体。引入间隔物
• The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications
  作者：Pavel I. Kitov、Craig Railton、David R. Bundle

  DOI：10.1016/s0008-6215(98)00053-6

  日期：1998.2

  The P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from <i>Shigella dysenteriae</i> Type 9 in the Form of Its Methyl (<i>R</i>)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside
  作者：Samarpita Roy、Nirmolendu Roy

  DOI：10.1081/car-120026456

  日期：2003.12.31

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.
• Maeda, Hirokazu; Ishida, Hideharu; Kiso, Makoto, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 369 - 386
  作者：Maeda, Hirokazu、Ishida, Hideharu、Kiso, Makoto、Hasegawa, Akira

  DOI：——

  日期：——
• Examination of the Biological Role of the α(2→6)-Linked Sialic Acid in Gangliosides Binding to the Myelin-Associated Glycoprotein (MAG)
  作者：Oliver Schwardt、Heiko Gäthje、Angelo Vedani、Stefanie Mesch、Gan-Pan Gao、Morena Spreafico、Johannes von Orelli、Sørge Kelm、Beat Ernst

  DOI：10.1021/jm801058n

  日期：2009.2.26

  The tetrasaccharide 1, a substructure of ganglioside GQ1b alpha, shows a remarkable affinity for the myelin-associated glycoprotein (MAG) and was therefore selected as starting point for a lead optimization program. In our search for structurally simplified and pharmacokinetically improved mimics of 1, modifications of the core disaccharide, the alpha(2 -> 3)- and the alpha(2 -> 6)-linked sialic acid were synthesized. Biphenylmethyl and (S)-lactate were identified as suitable replacements for the alpha(2 -> 6)-linked sialic acid. Combined with a core modification and the earlier found aryl amide substituent in the 9-position of the alpha(2 -> 3)-linked sialic acid, high affinity MAG antagonists were identified. All mimics were tested in a competitive target-based binding assay, providing relative inhibitory potencies (rlP). Compared to the reference tetrasaccharide 1, the rIPs of the most potent antagonists 59 and 60 are enhanced nearly 400-fold. Their K(D)s determined in surface plasmon resonance experiments are in the low micromolar range. These results are in semiquantitative agreement with molecular modeling studies. This new class of glycomimetics will allow to validate the role of MAG in the axon regeneration process.