2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 617691-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: 2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(2-hydroxyethoxy)oxan-2-yl]methyl acetate
• CAS: 617691-71-1
• 化学式: C₁₆H₂₄O₁₁
• 分子量: 392.36
• InChiKey: FGWDENPSBRTVSA-OWYFMNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal 甲醇 、 sodium azide 、 水 、 氢气 、 sodium methylate 、 乙酸酐 、 sodium hydride 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成
  参考文献：
  名称：

  Application of the four-component Ugi condensation for the preparation of sulfated glycoconjugate libraries

  摘要：

  A focused library of novel, sulfated glycoconjugates was synthesized by utilizing carbohydrate-derived blocks in the four-component Ugi condensation. Library members comprise a sulfated monosaccharide linked by various spacers to either in aromatic or monosulfated moiety, or a second sulfated monosaccharide. The affinities of these heparan sulfate (HS) mimetics for the HS-binding fibroblast growth factors FGF-1 and FGF-2 were measured via a surface plasmon resonance solution affinity assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.017
• 作为产物：
  描述：

  propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 喹啉 、 Lindlar's catalyst 、 氢气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  通过连续分子内氢原子转移/分子间自由基烯丙基化反应在碳水化合物系统中形成 CC 键

  摘要：

  这项工作得到了德国科学与创新部长的 Gobierno de Canarias 研究计划 (SolSubC200801000192 和 CTQ2010-18244) 的支持，并由 Fondo Europeo de Desarrollo 地区 (FEDER) 共同资助。IP-M。感谢西班牙部长级 Ciencia e Innovacion 的研究计划 PIE 200930I138。LMQ 感谢 Consejo Superior de Investigaciones Cientificas (CSIC)（I3P 计划）提供的奖学金。

  DOI：

  10.1002/ejoc.201200300

文献信息

• One-pot synthesis of multivalent arrays of mannose mono- and disaccharides
  作者：Wayne Hayes、Helen M.I Osborn、Sadie D Osborne、Robert A Rastall、Barbara Romagnoli

  DOI：10.1016/j.tet.2003.08.011

  日期：2003.9

  The synthesis of a selection of multivalent arrays of mannose mono- and disaccharides, that are of potential use as anti-infective agents against enterobacteria infections, is described.

  描述了多种甘露糖单糖和二糖多价阵列的合成，其可能用作抗肠杆菌感染的抗感染剂。
• Carbohydrate-Coated Supramolecular Structures:  Transformation of Nanofibers into Spherical Micelles Triggered by Guest Encapsulation
  作者：Ja-Hyoung Ryu、Eunji Lee、Yong-beom Lim、Myongsoo Lee

  DOI：10.1021/ja070173p

  日期：2007.4.1

  rigid-flexible dendritic block molecules consisting of a rigid aromatic segment as a stem segment, carbohydrate-branched dendrons as a flexible head, and a hydrophobic alkyl chain were synthesized and characterized. The carbohydrate conjugate molecule based on a methyl group as a hydrophobic tail, in the solid state, self-assembles into a 1D nanostructure, whereas the molecule based on a longer hydrophobic

  合成并表征了由刚性芳族链段作为茎段、碳水化合物支化树突作为柔性头和疏水性烷基链组成的三嵌段刚柔树突状嵌段分子。X 射线散射证实，基于甲基作为疏水尾部的碳水化合物共轭分子在固态下自组装成一维纳米结构，而基于较长疏水尾部的分子自组装成二维纳米片. 然而，在水溶液中，正如动态光散射和透射电子显微镜 (TEM) 研究证实的那样，观察到两种分子自组装成具有均匀直径的碳水化合物涂层圆柱形聚集体。值得注意的是，这些圆柱形物体在添加客体分子后可逆地转变为球形物体。碳水化合物涂层纳米结构与大肠杆菌细胞相互作用的研究表明，两种纳米物体都可以固定细菌细胞，而固定程度显着取决于纳米结构的形状。这些结果表明，对外部刺激有反应的超分子材料可以为控制许多生物活动提供新的机会。
• Process for the production of peracylated 1-0-glycosides
  申请人：Schering AG

  公开号：US20030069402A1

  公开（公告）日：2003-04-10

  The invention relates to a process for the production of peracylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar is a monosaccharide that is functionalized in 1-OH-position, R represents methyl, ethyl, propyl, isopropyl, tbutyl, phenyl, n means 2, 3 or 4, X means —COO— or —NH—and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of peracylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  该发明涉及一种生产通式I的过酰化1-O-糖苷或其盐的工艺，其中糖是在1-OH位置上被官能化的单糖，R代表甲基、乙基、丙基、异丙基、叔丁基、苯基，n取2、3或4，X代表—COO—或—NH—，L代表一条直链、分支、饱和或不饱和的C1-C30碳链，该碳链可以被基团中断或取代。根据该发明的工艺从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产具有1-O官能化侧链的过酰化糖苷。
• 2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands
  作者：Li-Ying Yang、Yuki Kawada、Lina Bai、Daijiro Kubota、Hideya Yuasa

  DOI：10.1039/c1ob05775h

  日期：——

  The synthesis of bioactive oligosaccharides is too tedious to scale up for commercialization. However, structurally simplified glycomimetics are commercializable, if they can be synthesized much more easily than the oligosaccharides while having a comparable bioactivity. In this study, we propose a 2-oxabutane (OB) structure as an imitation of the internal monosaccharide units in oligosaccharides. Two trimannoside and three pentamannoside OB-glycomimics were synthesized in remarkably short steps. Among them, Manα1-OB-2Man 10, a trimannoside mimic, showed eight-fold affinity toward concanavalin A (ConA) relative to methyl mannoside in latex agglutination lectin assay and equilibrium dialysis assay (EDA), while the other mimics showed three- to four-fold affinities. EDA indicated that the bindings between each mimic molecule and a ConA subsite were all in one-to-one stoichiometry and thus these mimics were monovalent ligands, excluding multivalence effect for the high affinities. The strong affinity of 10 could be explained by the occupation of two mannose binding sites of a ConA subsite by its two mannose units. Mimic 10 proved to be even a better ligand for ConA than the natural disaccharide Manα1,2Man, while been much more easy to synthesize, thereby illustrating the potential of the approach here presented.

  生物活性低聚糖的合成过于繁琐，无法扩大商业化规模。然而，如果结构简化的拟糖类化合物能比低聚糖更容易合成，同时又具有相当的生物活性，那么它们是可以商业化的。在这项研究中，我们提出了一种 2-氧杂丁烷（OB）结构，作为低聚糖内部单糖单元的仿生结构。我们在极短的时间内合成了两种三单糖苷和三种五单糖苷的 OB-甘聚物。其中，Manα1-OB-2Man 10 是一种三单糖苷模拟物，在胶乳凝集凝集素试验和平衡透析试验（EDA）中，它对 concanavalin A（ConA）的亲和力是甲基甘露糖苷的八倍，而其他模拟物的亲和力为三至四倍。EDA 表明，每个模拟物分子与一个 ConA 亚位点之间的结合都是一一对应的，因此这些模拟物是单价配体，排除了高亲和力的多价效应。10 的强亲和力可解释为其两个甘露糖单位占据了 ConA 位点的两个甘露糖结合位点。事实证明，与天然二糖 Manα1,2Man 相比，模拟 10 甚至是更好的 ConA 配体，而且更容易合成，从而说明了本文所介绍方法的潜力。
• Water-soluble photoluminescent <scp>d</scp>-mannose and <scp>l</scp>-alanine functionalized silicon nanocrystals and their application to cancer cell imaging
  作者：Yi Zhai、Mita Dasog、Ryan B. Snitynsky、Tapas K. Purkait、Maryam Aghajamali、Allison H. Hahn、Christopher B. Sturdy、Todd L. Lowary、Jonathan G. C. Veinot

  DOI：10.1039/c4tb01161a

  日期：——

  Mannose and alanine functionalized SiNPs have been synthesized, and these particles were evaluated as luminescent agents for imaging MCF-7 cells.

  甘露糖和丙氨酸功能化的SiNPs已经合成，这些颗粒被评估为成像MCF-7细胞的发光剂。