1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖 | 13100-46-4

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 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
• 中文名称: 1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖
• 中文别名: 2,3,4,6-四邻乙酰基-beta-d-吡喃葡萄糖；1,2,3,4-四-O-乙酰基-β-D-吡喃葡萄糖；1,2,3,4-四-邻-乙酰基-beta-d-吡喃(型)葡萄糖；1,2,3,4-四-O-乙酰基-Β-D-吡喃葡萄糖
• 英文名称: 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: β-D-glucose 1,2,3,4-tetraacetate；1,2,3,4-tetra-O-acetyl-β-D-glucopyranoside；1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranose；[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 13100-46-4
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: FEQXFAYSNRWXDW-RKQHYHRCSA-N

物化性质

• 熔点：
  126-128 °C(lit.)
• 沸点：
  0.120 °C(Press: 0.0001 Torr)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿
• LogP：
  1.140 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  29400090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途
经证实，该磷酰化衍生物在肌醇合成酶的底物研究中表现出很高的价值，并且还在阴离子表面活性剂的制备中发挥了重要作用。

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖 在 硼氘化钠 、 β-glucosidase 、 水 作用下， 以 甲醇 、 二氯甲烷 、 重水 为溶剂， 生成 异丙基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  溶剂和α-二次动力学同位素对β-葡萄糖苷酶的影响

  摘要：

  来自甜杏仁的β-葡萄糖苷酶是保留的家族1，糖水解酶。已知通过芳基葡糖苷进行的酶的糖基化几乎没有酸催化发生。对于该反应，溶剂和α-二次动力学同位素效应均为1.0。但是，对于脱葡萄糖基化反应（例如，k cat代表2,4-二硝基苯基-β - D-吡喃葡萄糖苷），溶剂氘的同位素同位素效应较小，为1.50（±0.06），α二次动力学同位素效应约为1.12（± 0.03）。对于芳基葡糖苷，K猫/ K中号是的pK非常敏感一个酚离去基团[β的LG  ≈ - 1; Dale等，生物化学 25（1986）2522–2529]。对于烷基葡糖苷，β1g较小（介于-0.2和-0.3之间），但仍为负值。加上小溶剂同位素对不依赖pH值的二阶速率常数的影响，该常数依赖于2,2,2-三氟乙基-β-葡萄糖苷[ D2O（k cat / K M）= 1.23（±0.04）]表示在烷基糖苷水解的过渡态中，糖苷元-糖苷配基键裂比糖苷

  DOI：

  10.1016/j.bbapap.2015.02.015
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 吡啶 、 氢溴酸 、 溶剂黄146 作用下， 反应 12.01h， 生成 1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖
  参考文献：
  名称：

  Self-Assembly of β-Glucosidase and d-Glucose-Tethering Zeolite Crystals into Fibrous Aggregates

  摘要：

  beta -Glucosidase and D-glucose-tethering micrometer-sized zeolite crystals self-assemble into thin (2-20 mum) and very long (>1 cm) fibrous aggregates in water. The process proceeds at a faster rate in a buffer solution of pH 4.8 at which the enzymatic activity is highest. The zeolite and enzyme remain intact within the fibrous material. Furthermore, the enzymatic activity of beta -glucosidase is preserved even after they are kept in water for more than 6 months at room temperature. With the zeolite to enzyme weight ratio of 5, all the zeolite crystals are buried within the round fibrils which consist of either a single strand or helical double strands. Upon increasing the ratio to 10, clusters of unburied zeolite crystals appear on the exterior of the fibrils, while narrow flat fibers with smooth surfaces are formed upon decreasing the ratio to 2.5. The process is proposed to initiate by the tight binding between the zeolite-bound D-glucose moieties and beta -glucosidase followed by crystallization of the enzyme over the zeolite-bound enzyme monolayer. This report thus reveals a novel behavior of beta -glucosidase and demonstrates an unprecedented phenomenon that an enzyme and its substrate-tethering inorganic crystals self-assemble into structured aggregates.

  DOI：

  10.1021/ja0028222

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• 2-<i>O</i>-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation
  作者：Julia Weber、Dennis Svatunek、Simon Krauter、Gregor Tegl、Christian Hametner、Paul Kosma、Hannes Mikula

  DOI：10.1039/c9cc07194f

  日期：——

  idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O-2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1,2-trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.

  通过恢复一个古老的想法，我们证明了烷氧基羰基可用于糖基化反应，以通过在O -2处的碳酸酯部分的参与来实现完全的立体控制。制备了各种苄氧羰基保护的糖基供体，并将其用于对碱不稳定的化合物进行有效的1，2-反式糖基化和糖基酯的合成。
• [EN] 4-BIARYLYL-1-PHENYLAZETIDIN-2-ONES<br/>[FR] 4-BIARYLYL-1-PHÉNYLAZÉTIDIN-2-ONES
  申请人：MICROBIA INC

  公开号：WO2005047248A1

  公开（公告）日：2005-05-26

  4-Biarylyl-1-phenylazetidin-2-ones useful for the treatment of hypercholesterolemia are disclosed. The compounds are of a general formula (I) in which formula (II) represents an aryl or heteroaryl residue, Ar represents an aryl residue; U is a two to six atom chain; and the R’s represent substituents.

  4-双苯基-1-苯基氮杂环丁烷-2-酮，用于治疗高胆固醇血症的化合物被披露。这些化合物具有通用公式(I)，其中公式(II)代表一个芳基或杂芳基残基，Ar代表一个芳基残基；U是2到6个原子的链；而R's代表取代基。
• Linking of Alcohols with Vinyl Azides
  作者：Yi-Feng Wang、Ming Hu、Hirohito Hayashi、Bengang Xing、Shunsuke Chiba

  DOI：10.1021/acs.orglett.6b00116

  日期：2016.3.4

  A protocol to link alcohols with vinyl azides has been established through fluoro- or bromo-alkoxylation of vinyl azides to provide α-alkoxy-β-haloalkyl azides. A series of primary and secondary alcohols including natural products and their derivatives such as sugars and steroids were successfully anchored with vinyl azides. The as-prepared cyanine dye linked testosterones were capable of rapid cell

  通过乙烯基叠氮化物的氟-或溴-烷氧基化以提供α-烷氧基-β-卤代烷基叠氮化物，已经建立了将醇与乙烯基叠氮化物连接的方案。包括天然产物及其衍生物（如糖和类固醇）在内的一系列伯醇和仲醇已成功地与乙烯基叠氮化物固定在一起。所制备的花青染料连接的睾丸激素能够实时快速进行细胞膜成像。
• Hexafluoroisopropyl Sulfamate: A Useful Reagent for the Synthesis of Sulfamates and Sulfamides
  作者：Matthew A. Sguazzin、Jarrod W. Johnson、Jakob Magolan

  DOI：10.1021/acs.orglett.1c00855

  日期：2021.5.7

  Sulfamates and sulfamides are most often synthesized from alcohols and amines with sulfamoyl chloride, which is an unstable reagent. We have identified hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcohols, amines, phenols, and anilines under mild reaction conditions. The sole byproduct of the reaction is hexafluoroisopropanol (HFIP) and reaction

  氨基磺酸盐和磺酰胺最经常是由醇和胺与氨磺酰氯合成的，氨磺酰氯是不稳定的试剂。我们已经确定六氟异丙基氨基磺酸盐（HFIPS）是一种稳定的固体，在温和的反应条件下，它很容易与多种醇，胺，酚和苯胺反应。反应的唯一副产物是六氟异丙醇（HFIP），在进行水后处理（可选）并通过蒸发除去溶剂后，通常可以高纯度分离反应产物。