2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde | 181629-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde
• 英文别名: 2-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]acetaldehyde
• CAS: 181629-23-2
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: FLEOMTFUABHNQX-UMUOWMJJSA-N

物化性质

• 沸点：
  585.9±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde 在 N-甲基吗啉 、 lithium hydroxide 、 sodium tetrahydroborate 、 magnesium sulfate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1
• 作为产物：
  描述：

  3-(α-L-fucopyranosyl)-prop-1-ene 在 二甲基硫 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 39.0h， 生成 2-(tri-O-benzyl-α-L-fucopyranosyl)-acetaldehyde
  参考文献：
  名称：

  Design and synthesis of C-linked fucosides as inhibitors of E-selectin

  摘要：

  Two series of C-linked fucosides as mimetics for the tetrasaccharide sialyl Lewis X have been synthesized and tested as inhibitors of E-Selectin. The fucopeptides have been prepared from three key intermediates, including alpha-C-allyl fucose, natural and unnatural amino acids bearing hydroxyl groups and an alpha,omega-diacid moiety for the imitation of the essential three parts of SLe(x), i.e., the Fuc, Gal, and NeuAc. The nature and distance of the linkage of the fucose moiety to the amino acids as well as the distance between the amino acids and the terminal carboxylic acid group turned out to be crucial for the biological activity. In addition the necessity of both OH groups (4- and 6-OH) in the Gal part could be confirmed. Conformational NMR study of the most active mimetic supports the structure-activity relationship. A second series of mimetics was prepared, where Fuc and Gal moieties were purely C-linked. In the synthesis of beta-C-allyl galactose an intramolecular 1,2-hydride shift led to an interesting side product. However, the substituted glycosidic oxygens led to a substantial loss of conformational constrain, which could not be compensated and resulted in low activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00127-7

文献信息

• Design, synthesis and biological evaluation of aryl-substituted sialyl Lewis X mimetics prepared via cross-metathesis of C-fucopeptides
  作者：Christoph M Huwe、Thomas J Woltering、Jan Jiricek、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1016/s0968-0896(98)00245-4

  日期：1999.5

  been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and > 1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed

  已经开发了几种芳基取代的C-岩藻肽作为唾液酸化的路易斯X模拟物。尽管与SLe（x）相比，这些化合物的结构要简单得多，但观察到的对E-选择素的结合亲和力高达3倍，对P-选择素的结合亲和力高达1000倍。此外，介绍了在台式条件下使用钌催化的交叉烯烃复分解反应在合成的非常后期从SLe（x）模拟模板生成许多类似物的便捷策略。
• An approach to stereoselective preparation of 3-C-glycosylated d- and l-glucals
  作者：Kamil Parkan、Lukáš Werner、Zuzana Lövyová、Eva Prchalová、Ladislav Kniežo

  DOI：10.1016/j.carres.2009.11.025

  日期：2010.2

  corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl

  描述了一种从相应的α-或β-甘露聚糖核糖体开始立体选择性合成α-或β-3-C-糖基化的L-或D-1,2-葡萄糖的方法。该方法的关键步骤是衍生自扁桃酸两个对映异构体的手性乙烯基醚的立体选择性环加成反应。1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3-C-[（2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖基）甲基] -L-阿拉伯-己-1-烯醇，1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3-C-[（2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖基）甲基] -D-阿拉伯糖基-己-1-烯醇和1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3- C-[（2,3,4-三-O-苄基-α-L-呋喃核糖基）甲基] -D-阿拉伯糖基己基-1-烯醇用作该方法的一个实例。
• Asymmetric Strecker Synthesis of C-Glycopeptide
  作者：Stéphane P. Vincent、Axel Schleyer、Chi-Huey Wong

  DOI：10.1021/jo000034p

  日期：2000.7.1
• Synthesis of sialyl Lewis X mimetics using the Ugi four-component reaction
  作者：Chung-Ying Tsai、William K.C. Park、Gabriele Weitz-Schmidt、Beat Ernst、Chi-Huey Wong

  DOI：10.1016/s0960-894x(98)00422-3

  日期：1998.9

  Application of the Ugi four-component condensation to rapidly synthesize a library of glycopeptide mimics of the tetrasaccharide SLe(x) as inhibitors of E- and P-selectin, and to study the effect of varied functionality in mimics on the inhibition is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Solid-phase supported mimic of GDP-l-galactose
  作者：Barbara La Ferla、Laura Russo、Cristina Airoldi、Francesco Nicotra

  DOI：10.1016/j.tetasy.2009.03.005

  日期：2009.5

  A C-glycoside mimetic of L-galactose 1-diphosphate, a potential ligand of GDP-L-galactose hydrolase, an enzyme involved in the biosynthesis of vitamin C, has been designed, stereoselectively synthesised by C-allylation of tribenzylated L-fucose, by periodate-osmium tetroxide degradation of the double bond, by condensation of the obtained aldehydes with benzylacetate and by deprotection. The obtained mimetic was linked to a sepharose resin. (C) 2009 Elsevier Ltd. All rights reserved.