2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose | 42390-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose
• 英文别名: 2,3,4,6,2',3',4',6'-octakis-O-(trimethylsilyl)-α,α-trehalose；2,3,4,6-tetrakis-O-(trimethylsilyl)-α-D-glucopyranosyl-2,3,4,6-tetrakis-O-(trimethylsilyl)-α-D-glucopyranoside；Trimethylsilyl-D-(+)-trehalose；trimethyl-[[(2R,3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-[(2R,3R,4S,5R,6R)-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]silane
• CAS: 42390-78-3
• 化学式: C₃₆H₈₆O₁₁Si₈
• 分子量: 919.756
• InChiKey: YQFZNYCPHIXROS-XPMTUQOHSA-N

物化性质

• 保留指数：
  2850.1;2722

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose 在 N-乙基吗啉 、 水 、 potassium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 [3,4,5-三羟基-6-[3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-四氢吡喃-2-基]甲氧基膦酸
  参考文献：
  名称：

  克级合成的α，α-海藻糖6-单磷酸酯和α，α-海藻糖6,6'-二磷酸酯。

  摘要：

  DOI：

  10.1016/0008-6215(94)84050-4
• 作为产物：
  描述：

  海藻糖 以90%的产率得到2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose
  参考文献：
  名称：

  海藻糖6-单和6,6'-双链霉烯酸酯及相关酯的合成方法改进

  摘要：

  通过在二环己基碳二亚胺存在下将（羟基保护的）酸偶合到部分三甲基甲硅烷基化的糖上，可以简化α-，α-海藻糖和相关化合物的6-单-和6,6'-二-胭脂红酸酯的合成和4-二甲基氨基吡啶。（2-RS，3-RS）-3-羟基-2-十四烷基十五烷酸（DL-二十二烷酸）及其2RS，3SR非对映异构体是由棕榈酸甲酯通过连续Claisen缩合，还原，色谱分离和分离而制得的酸性反应物。皂化。与叔丁基氯二甲基硅烷（咪唑）反应，得到二取代的醚酯，通过部分水解将其转化为所需的3-叔丁基二甲基甲硅烷基醚。通过RS的反应获得了6联单硬脂酸高收率（78％），SR酸具有已知的七-O-（三甲基甲硅烷基）海藻糖，并且从等摩尔部分的RS，RS酸和六-O-（三甲基甲硅烷基）海藻糖获得高收率。过量（2.5摩尔份）的RS，RS酸得到6，6′-二酯（69％）。类似地，从（Me 3 Si）6-海藻糖获得单和双棕榈酸酯。单（RS，RS）-（Me

  DOI：

  10.1016/0008-6215(91)84089-w

文献信息

• Simple one-pot regioselective 6-O-phosphorylation of carbohydrates and trehalose desymmetrization
  作者：A. Abragam Joseph、Chun-Wei Chang、Cheng-Chung Wang

  DOI：10.1039/c3cc47180b

  日期：——

  Biologically essential carbohydrate 6-phosphates, especially trehalose 6-phosphate, can be synthesized easily in excellent overall yields in 2 steps involving minimum protecting group manipulations. We can cleave the diphenylphosphate group for further synthetic objectives.

  生物学上必需的碳水化合物6-磷酸，特别是海藻糖6-磷酸，可以通过涉及最少保护基团操作的两步反应，在优异的整体产率下轻松合成。我们可以裂解二苯基磷酸酯基团以实现进一步的合成目标。
• Time-Dependent Profiling of Metabolites from Snf1 Mutant and Wild Type Yeast Cells
  作者：Elizabeth M. Humston、Kenneth M. Dombek、Jamin C. Hoggard、Elton T. Young、Robert E. Synovec

  DOI：10.1021/ac800998j

  日期：2008.11.1

  The effect of sampling time in the context of growth conditions on a dynamic metabolic system was investigated in order to assess to what extent a single sampling time may be sufficient for general application, as well as to determine if useful kinetic information could be obtained. A wild type yeast strain (W) was compared to a snf1Δ mutant yeast strain (S) grown in high-glucose medium (R) and in low-glucose medium containing ethanol (DR). Under these growth conditions, different metabolic pathways for utilizing the different carbon sources are expected to be active. Thus, changes in metabolite levels relating to the carbon source in the growth medium were anticipated. Furthermore, the Snf1 protein kinase complex is required to adapt cellular metabolism from fermentative R conditions to oxidative DR conditions. So, differences in intracellular metabolite levels between the W and S yeast strains were also anticipated. Cell extracts were collected at four time points (0.5, 2, 4, 6 h) after shifting half of the cells from R to DR conditions, resulting in 16 sample classes (WR, WDR, SR, SDR) × (0.5, 2, 4, 6 h). The experimental design provided time course data, so temporal dependencies could be monitored in addition to carbon source and strain dependencies. Comprehensive two-dimensional (2D) gas chromatography coupled to time-of-flight mass spectrometry (GC × GC-TOFMS) was used with discovery-based data mining algorithms (Anal. Chem. 2006, 78, 5068–5075 (ref 1); J. Chromatogr., A 2008, 1186, 401–411 (ref 2)) to locate regions within the 2D chromatograms (i.e., metabolites) that provided chemical selectivity between the 16 sample classes. These regions were mathematically resolved using parallel factor analysis to positively identify the metabolites and to acquire quantitative results. With these tools, 51 unique metabolites were identified and quantified. Various time course patterns emerged from these data, and principal component analysis (PCA) was utilized as a comparison tool to determine the sources of variance between these 51 metabolites. The effect of sampling time was investigated with separate PCA analyses using various subsets of the data. PCA utilizing all of the time course data, averaged time course data, and each individual time point data set independently were performed to discern the differences. For the yeast strains examined in the current study, data collection at either 4 or 6 h provided information comparable to averaged time course data, albeit with a few metabolites missing using a single sampling time point.

  在动态代谢系统的背景下，研究了采样时间在生长条件下的影响，以评估在一般应用中单一采样时间可能足够到何种程度，以及是否可以获得有用的动力学信息。将野生型酵母菌株（W）与snf1Δ突变型酵母菌株（S）在高葡萄糖培养基（R）和含乙醇的低葡萄糖培养基（DR）中进行比较。在这些生长条件下，预计会激活利用不同碳源的不同代谢途径，因此预期与生长培养基中碳源相关的代谢物水平会发生变化。此外，Snf1蛋白激酶复合体是适应细胞代谢从发酵R条件到氧化DR条件所必需的，因此也预期W和S酵母菌株之间的胞内代谢物水平存在差异。在将一半细胞从R条件转移到DR条件后的四个时间点（0.5、2、4、6小时）收集细胞提取物，产生了16个样本类别（WR、WDR、SR、SDR）×（0.5、2、4、6小时）。实验设计提供了时间进程数据，因此除了碳源和菌株依赖性外，还可以监测时间依赖性。综合二维（2D）气相色谱与飞行时间质谱（GC×GC-TOFMS）结合基于发现的挖掘算法（《分析化学》2006，78，5068–5075（参考文献1）；《色谱A》2008，1186，401–411（参考文献2））用于在2D色谱图中定位在16个样本类别之间提供化学选择性的区域（即代谢物）。这些区域通过平行因子分析进行数学解析，以正向鉴定代谢物并获取定量结果。利用这些工具，识别并定量了51种独特代谢物。这些数据中出现了各种时间进程模式，并利用主成分分析（PCA）作为比较工具来确定这51种代谢物之间的变异来源。通过使用数据的不同子集进行单独的PCA分析，研究了采样时间的影响。利用所有时间进程数据、平均时间进程数据以及每个独立时间点数据集分别进行了PCA分析，以辨别差异。对于当前研究中考察的酵母菌株，在4或6小时收集数据提供的信息与平均时间进程数据相当，尽管使用单一采样时间点时会缺失一些代谢物。
• [EN] BIODEGRADABLE TREHALOSE GLYCOPOLYMERS<br/>[FR] GLYCOPOLYMÈRES BIODÉGRADABLES DE TRÉHALOSE
  申请人：UNIV CALIFORNIA

  公开号：WO2016025668A1

  公开（公告）日：2016-02-18

  Structures and methods of making biodegradable trehalose co-polymers are disclosed. Specifically, biodegradable trehalose co-polymers consist of the general structure R5-[R1R2C - CR3R4]n-[DG]m-R6, wherein R1-R4 are independently selected from hydrogen or a side chain comprising at least one carbon atom, and wherein at least one of R1-R4 is a side chain comprising -L-trehalose, wherein L is a linker molecule that links trehalose to the monomer through at least one of the trehalose hydroxyl groups (-OH), wherein DG is a biodegradable group, and wherein R5 and R6 are end groups.

  生物可降解海藻糖共聚物的结构和制备方法被披露。具体来说，生物可降解海藻糖共聚物由一般结构R5-[R1R2C - CR3R4]n-[DG]m-R6组成，其中R1-R4独立地选自氢或包含至少一个碳原子的侧链，且R1-R4中至少有一个是包含-L-海藻糖的侧链，其中L是将海藻糖通过至少一个海藻糖羟基（-OH）连接到单体的连接分子，DG是一个生物可降解基团，R5和R6是末端基团。
• Nanolipid-Trehalose Conjugates and Nano-Assemblies as Putative Autophagy Inducers
  作者：Eleonora Colombo、Michele Biocotino、Giulia Frapporti、Pietro Randazzo、Michael S. Christodoulou、Giovanni Piccoli、Laura Polito、Pierfausto Seneci、Daniele Passarella

  DOI：10.3390/pharmaceutics11080422

  日期：——

  The disaccharide trehalose is an autophagy inducer, but its pharmacological application is severely limited by its poor pharmacokinetics properties. Thus, trehalose was coupled via suitable spacers with squalene (in 1:2 and 1:1 stoichiometry) and with betulinic acid (1:2 stoichiometry), in order to yield the corresponding nanolipid-trehalose conjugates 1-Sq-mono, 2-Sq-bis and 3-Be-mono. The conjugates were assembled to produce the corresponding nano-assemblies (NAs) Sq-NA1, Sq-NA2 and Be-NA3. The synthetic and assembly protocols are described in detail. The resulting NAs were characterized in terms of loading and structure, and tested in vitro for their capability to induce autophagy. Our results are presented and thoroughly commented upon.

  葡萄糖二糖海藻糖是一种自噬诱导剂，但由于其糟糕的药代动力学特性，其药理应用受到严重限制。因此，通过适当的间隔物，将海藻糖与角鲨烯（1:2和1:1的化学计量比）和与萜酸（1:2的化学计量比）偶联，以产生相应的纳米脂质-海藻糖共轭物1-Sq-mono，2-Sq-bis和3-Be-mono。这些共轭物被组装成相应的纳米组装体（NAs）Sq-NA1，Sq-NA2和Be-NA3。详细描述了合成和组装方案。所得的NAs根据载荷和结构进行表征，并在体外测试其诱导自噬的能力。我们将展示并对结果进行详细评论。
• Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides
  作者：Yann Bourdreux、Aurélie Lemétais、Dominique Urban、Jean-Marie Beau

  DOI：10.1039/c0cc04398b

  日期：——

  Tandem catalysis by using iron(III) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.

  通过使用六水合氯化铁（III）进行串联催化可导致碳水化合物构件显示出正交的保护基团模式，如海藻糖和麦芽糖二糖的区域选择性保护所示。