(R)-((2,3-双(十六烷氧基)丙氧基)甲基)苯 | 13071-57-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: (R)-((2,3-双(十六烷氧基)丙氧基)甲基)苯
• 英文名称: (R)-((2,3-bis(hexadecyloxy)propoxy)methyl)benzene
• 英文别名: (2R)-3-benzyloxy-1,2-di-hexadecyloxypropane；1,2-di-O-n-hexadecyl-3-O-benzyl-sn-glycerol；3-O-Benzyl-1,2-di-O-hexadecyl-sn-glycerol；1,2-di-O-hexadecyl-3-O-benzyl-sn-glycerol；[(2R)-2,3-dihexadecoxypropoxy]methylbenzene
• CAS: 13071-57-3
• 化学式: C₄₂H₇₈O₃
• 分子量: 631.08
• InChiKey: PTVZJDJWPQUMSK-HUESYALOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  45
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-((2,3-双(十六烷氧基)丙氧基)甲基)苯 在 钯 氢气 、 乙醇 、 silica gel 、 EtOAc light petroleum 作用下， 以 溶剂黄146 、 乙醇 为溶剂， 反应 3.0h， 以afforded the title compound 2.2 (1.44 g, 2.66 mmol, 71%) as a white powder的产率得到1,2-o-二十六基-sn-甘油
  参考文献：
  名称：

  ANALOGUES OF PHOSPHATIDYLINOSITOL MANNOSIDES

  摘要：

  本发明涉及免疫调节化合物，特别是能够诱导IL-12分泌的化合物。本发明还涉及包含这些化合物、前体和前药的组合物，这些化合物作为疫苗佐剂的使用，以及这些化合物用于治疗与感染、特应性疾病或癌症相关的疾病或病症的使用。

  公开号：

  US20100297156A1
• 作为产物：
  描述：

  (R)-(+)-3-苄氧基-1,2-丙二醇 、 溴代十六烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 以43%的产率得到(R)-((2,3-双(十六烷氧基)丙氧基)甲基)苯
  参考文献：
  名称：

  WO2008/75983

  摘要：

  公开号：

文献信息

• [DE] ANTIADHÄSIVE SULFATID-MIMETIKA<br/>[EN] ANTI-ADHESIVE SULFATIDE ANALOGUES<br/>[FR] ANALOGUES ANTI-ADHESIFS DE SULFATIDES
  申请人：GLYCOREX AB

  公开号：WO1998030573A1

  公开（公告）日：1998-07-16

  (DE) Die Erfindung betrifft Mimetika der Formel (I) der sogenannten Sulfatide (3-O-sulfatierte Galactosylceramide), bei denen das natürliche Ceramid durch eine einfache dialkylierte Einheit substituiert ist. Die Anknüpfung dieses Aglycons kann sowohl O-, S- oder C-glycosidisch erfolgen. Des weiteren können diese Mimetika statt einer, auch mehrere Sulfat- oder andere saure Gruppen enthalten. Die Erfindung betrifft ausserdem die Herstellung dieser Verbindungen, deren Verwendung zur Herstellung von Arzneimitteln und Diagnostika. In der Formel (I) bedeuten R1, R2 unabhängig voneinander -(CH2)n-CH3, n eine ganze Zahl von 10 bis 30, R3-R6 unabhängig voneinander OH, OSO3H, OCH2COOH, CH(COOH)2, O(CH2)2CH(COOH)2 oder nicht-toxische Salze der entsprechenden Säuren, mit der Maßgabe, daß mindestens ein Rest R3-R6 ungleich OH ist, wobei die Hydroxy-Gruppen mit Schutzgruppen wie beispielsweise Benzyl, Benzyliden oder Isopropyliden versehen sei können, und X O, S, (CH2)2O oder CH2O.(EN) Analogues of formula (I) of the so-called sulfatides (3-O-sulphated galactosyl ceramides) are disclosed in which the natural ceramide is substituted by a simple dialkylated unit. This aglycone may be O-, S- or C-glycosidically linked. These analogues may also contain several sulphate or other acid groups instead of just one such group. Also disclosed is the preparation of these compounds and their use for producing medicaments and diagnostic agents. In the formula (I), R1, R2 independently represent -(CH2)n-CH3; n is an integer from 10 to 30; R3-R6 independently represent OH, OSO3H, OCH2COOH, CH(COOH)2, O(CH2)2CH(COOH)2 or non-toxic salts of the corresponding acids, provided that at least one radical R3-R6 be other than OH, and the hydroxy groups can be provided with protective groups such as benzyl, benzylidene or isopropylidene; and S stands for O, S, (CH2)2O or CH2O.(FR) L'invention concerne des analogues de formule (I) desdits sulfatides (galactosylcéramides 3-O-sulfatés) dans lesquels le céramide naturel est substitué par une unité dialkylée simple. Cet aglycone peut être relié O-, S- ou C-glycosidiquement. Ces analogues peuvent également contenir plusieurs groupes sulfates ou autres groupes acides, au lieu d'un seul groupe. L'invention concerne également la préparation de ces composés et leur utilisation pour préparer des médicaments et des agents de diagnostic. Dans la formule (I), R1, R2 désignent indépendamment -(CH2)n-CH3; n est un nombre entier de 10 à 30; R3-R6 désignent indépendamment OH, OSO3H, OCH2COOH, CH(COOH)2, O(CH2)2CH(COOH)2 ou des sels non toxiques des acides correspondants, à condition qu'au moins un des radicaux R3 à R6 soit différent de OH, les groupes hydroxyles pouvant être pourvus de groupes protecteurs tels que le benzyle, le benzylidène ou l'isopropylidène; et X désigne O, S, (CH2)2O ou CH2O.

  发明涉及一种称为(Ⅰ)的母式结构式所代表的三羟基 LackeOSylsodalite（Rangeolite-Ceramid）的类似物。其中，普通天然的 Ceramid 被一个简单的二元基团所取代。这种物质的连接方式可以是 O-、S- 或 C-glycOSidic。此外，这类物质也可以含有多个硫酸根或者其他酸性的组分。发明还涉及这些化合物的制备工作以及在 Compound 和诊断试剂方面的应用。 在母式结构式(I)中，R1、R2 分别代表独立的 -(CH2)n-CH3；n 是一个取值范围为 10 至 30 的整数；R3-R6 则代表独立的 OH、OSO3H、O COOH、CH(COOH)2、O( )2CH(COOH)2 或非剧毒酸对 应的盐。其中，必须至少有一个 R3-R6 不是羟基(OH)，羟基可以被结构性保护基团（如苯基、苯基双原子或异丙基双原子等）修饰。X代表 O、S、( )2O 或 O。
• Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues
  作者：RC Young、CP Downes、M Jones、KJ Milliner、KK Rana、JG Ward

  DOI：10.1016/0223-5234(94)90146-5

  日期：1994.1

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.
• Structure−Activity Relationships in Toll-like Receptor-2 Agonistic Diacylthioglycerol Lipopeptides
  作者：Wenyan Wu、Rongti Li、Subbalakshmi S. Malladi、Hemamali J. Warshakoon、Matthew R. Kimbrell、Michael W. Amolins、Rehman Ukani、Apurba Datta、Sunil A. David

  DOI：10.1021/jm901839g

  日期：2010.4.22

  The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.
• Short synthesis of sulfatide- and SQDG-mimetics as small molecular weight selectin inhibitors
  作者：Gerhard Kretzschmar、Alexander Toepfer、Michael Sonnentag

  DOI：10.1016/s0040-4020(98)00950-8

  日期：1998.12

  Small molecular weight sulfatide analogs were synthesised and tested in cell-based selectin mediated adhesion assays. The ceramide moiety of sulfatides could be replaced by simple glycerol ethers to obtain potent mimetics. The specific activity of these inhibitors towards P-selectin is illustrated by analogy with other polyanionic systems forming polyvalent arrays antagonising the polyanionic N-terminal binding sites of the dimeric PSGL-1 ligand. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of the Sialyl Lewis X Epitope Attached to Glycolipids with Different Core Structures and their Selectin-Binding Characteristics in a Dynamic Test System
  作者：Christian Gege、Jan Vogel、Gerd Bendas、Ulrich Rothe、Richard R. Schmidt

  DOI：10.1002/(sici)1521-3765(20000103)6:1<111::aid-chem111>3.0.co;2-x

  日期：2000.1.3

  Sialyl Lewis X (sLe(X))/selectin-mediated leukocyte rolling along endothelial cells has recently gained wide interest. In this paper the influence of the spacer length of laterally clustered neoglycolipids 1a-d on cell rolling in a dynamic test system is investigated. The required di-O-hexadecyl glycerols with none, and with three, six, or nine ethylene glycol units as spacer groups (compounds 4a-d) could be readily obtained. The synthesis of 1-O-thexyldimethylsilyl-protected sLe(X) 24 was based on sialylation of 2,3,4-O-unprotected galactose derivative 11 with sialyl phosphite 8 as donor; this afforded the desired disaccharide 12, which was transformed into trichloroacetimidate 14 as disaccharide donor. Reaction of 3-O-unprotected glucosamine derivative 18 with fucosyl donor 20 afforded disaccharide 21, which was transformed into the 4-O-unprotected derivative 23. Reaction of 14 with 23 furnished the desired tetrasaccharide 24 in good yield. Transformation of 24 into the trichloroacetimidate 26 as donor, followed by the reaction with 4a-d as acceptor gave, after deprotection, the target molecules 1a-d. For comparison, 4d was also connected with a sialyl residue (-->31) and with an N-acetylglucosamine residue (-->34). Compounds 1c and 1d with a hexaethylene glycol and a nonaethylene glycol spacer, respectively, were much more efficient in mediating selectin-dependent cell rolling in the dynamic test system than compounds 1a and 1b, which had no spacer (1a), or only a triethylene glycol spacer (1b).