1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucose | 10028-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucose
• 英文别名: 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose；1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranose；1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranose；O¹,O²,O³,O⁴-Tetraacetyl-O⁶-trityl-α-D-glucopyranose；(2R,3R,4S,5R,6R)-6-((Trityloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate；[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 10028-44-1
• 化学式: C₃₃H₃₄O₁₀
• 分子量: 590.627
• InChiKey: GTJGUFOLNHYRQE-VJLURNNQSA-N

物化性质

• 沸点：
  633.3±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucose 在 氢溴酸 、 溶剂黄146 作用下， 生成 1,2,3,4-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  1,2,3,4-Tetraacetyl-α-D-glucopyranose

  摘要：

  DOI：

  10.1021/ja01195a014
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 吡啶 作用下， 反应 12.0h， 生成 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-glucose
  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

• Synthesis of uniformly deuterated<i>n</i>-dodecyl-<i>β</i>-<scp>d</scp>-maltoside (<i>d</i>₃₉-DDM) for solubilization of membrane proteins in TROSY NMR experiments
  作者：Kazumi Hiruma-Shimizu、Arnout P. Kalverda、Peter J. F. Henderson、Steve W. Homans、Simon G. Patching

  DOI：10.1002/jlcr.3249

  日期：2014.12

  This work reports the first synthesis of uniformly deuterated n-dodecyl-β-d-maltoside (d39-DDM). DDM is a mild non-ionic detergent often used in the extraction and purification of membrane proteins and for solubilizing them in experimental studies of their structure, dynamics and binding of ligands. We required d39-DDM for solubilizing large α-helical membrane proteins in samples for [15N–1H]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d39-DDM used d7-d-glucose and d25-n-dodecanol to introduce deuterium labelling into both the maltoside and dodecyl moieties, respectively. Two glucose molecules, one converted to a glycosyl acceptor with a free C4 hydroxyl group and one converted to a glycosyl donor substituted at C1 with a bromine in the α-configuration, were coupled together with an α(1 → 4) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the α-configuration to give DDM. 1H NMR spectra were used to confirm a high level of deuteration in the synthesized d39-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.

  这项工作报告了均匀氘标记的n-十二烷基-β-d-麦芽糖苷（d39-DDM）的首次合成。DDM是一种温和的非离子型洗涤剂，通常用于膜蛋白的提取和纯化，以及在实验研究其结构、动力学和配体结合时的溶解。我们需要d39-DDM来溶解样品中的大型α-螺旋膜蛋白，以便进行[15N–1H]TROSY（横向弛豫优化光谱）NMR实验，从而实现最高的灵敏度和最佳的光谱分辨率。我们的d39-DDM合成使用了d7-d-葡萄糖和d25-n-十二醇，将氘标记引入麦芽糖苷和十二烷基基团中。两个葡萄糖分子，其中一个转化为具有自由C4羟基的糖苷受体，另一个转化为在C1位置被α-构型溴取代的糖苷供体，通过α(1→4)糖苷键结合在一起，形成麦芽糖，再通过用α-构型的C1溴取代将其与n-十二醇结合，得到DDM。利用1H NMR谱确认了合成的d39-DDM具有较高的氘标记水平，并展示其在消除52-kDa糖转运蛋白在DDM中溶解的TROSY NMR谱中的干扰信号方面的应用。
• Total synthesis of agalloside, isolated from Aquilaria agallocha, by the 5-O-glycosylation of flavan
  作者：Midori A. Arai、Yumi Yamaguchi、Masami Ishibashi

  DOI：10.1039/c7ob01004d

  日期：——

  Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic

  Agalloside（1）是我们小组使用固定化Hes1的珠子从沉香中分离得到的神经干细胞分化激活剂。我们进行agalloside（第一全合成1）经由5- ø的黄烷-glycosylation 25使用糖基氟化物20在BF的存在3 ·的Et 2 O.用DDQ随后的氧化，以黄烷酮2和脱保护依次agalloside提供（1）。该合成策略有望用于合成5- O-糖基化的类黄酮。合成的galloloside（1）加速了神经干细胞的分化，其结果可与天然化合物1媲美。
• SHORT SYNTHETIC PATHWAY FOR 1,6:2,3-DIANHYDRO-BETA-D-MANNOPYRANOSE
  申请人：Bouvenot Laurent

  公开号：US20110224446A1

  公开（公告）日：2011-09-15

  The invention relates to a method for preparing 1,6:2,3-dianhydro-β-D-mannopyranose and is characterized in that it includes a step of cyclizing the compound B, where R is an activating agent, in the presence of a base selected from among ammonium hydroxides and mineral bases.

  本发明涉及一种制备1,6:2,3-二去水-β-D-甘露糖苷的方法，其特征在于，它包括在氨水和矿物质碱中选择一种碱的存在下，将化合物B环化的步骤，其中R是一种活性剂。
• Verfahren zur Herstellung von 1,6-beta-D-Anhydroglucopyranose (Lävoglucosan) in hoher Reinheit
  申请人：SÜDZUCKER AKTIENGESELLSCHAFT MANNHEIM/OCHSENFURT

  公开号：EP0327920A2

  公开（公告）日：1989-08-16

  Die Erfindung betrifft ein Verfahren zur Herstellung von 1,6-ß-D-Anhydroglucopyranose (Levoglucosan) aus Stärke und/oder stärkehaltigem bzw. cellulosehaltigem Material durch Vakuumpyrolyse. Für eine groß-technische Herstellung von Levoglucosan in hoher Reinheit sind die bekannten Verfahren zu umständlich und/oder zu teuer. Bei der bekannten Stärkepyrolyse wird eine Vielzahl von Nebenprodukten gebildet, so daß langwierige Reinigungsverfahren unter Verwendung von organischen Lösungsmitteln und langsame Kristallisation üblich sind. Niedrige Ausbeuten und mangelnde Reinheit charakterisieren die bekannten Levoglucosan-Produkte. Es wird ein Verfahren zur Herstellung von Levoglucosan zur Verfügung gestellt, bei dem das Ausgangsmaterial mit einem auf max. 20 % eingestellten Wassergehalt depolymerisiert wird, die flüchtigen Bestandteile kondensiert werden und das Kondensat nach Neutralisation, Filtration und ggf. Behandlung mit einem Adsorptionsmittel, einer chromatographischen Trennung über lonenaustauscher, mit Wasser als Elutionsmittel, unterworfen und die Levoglucosan enthaltenden Fraktionen eingeengt und durch eine Verdampfungs- und/oder Kühlungskristallisation aus Wasser kristallines Levoglucosan erhalten wird.

  本发明涉及一种通过真空热解从淀粉和/或含淀粉或含纤维素的材料中生产 1,6-ß-D-脱水葡聚糖（左旋葡聚糖）的工艺。 已知的工艺过于复杂和/或过于昂贵，无法大规模生产高纯度的左旋葡聚糖。在已知的淀粉热解过程中，会产生大量的副产品，因此，使用有机溶剂进行冗长的提纯过程和缓慢的结晶过程十分常见。产量低、纯度低是已知左旋葡聚糖产品的特点。 本发明提供了一种生产左旋葡聚糖的工艺，在该工艺中，起始原料在含水量调整到最高 20% 的情况下进行解聚，挥发性成分被冷凝，冷凝物经过中和、过滤以及必要时的吸附剂处理后，用于生产左旋葡聚糖。使用吸附剂处理后，冷凝液通过离子交换器进行色谱分离，以水作为洗脱液，浓缩含左旋葡聚糖的馏分，通过蒸发和/或冷却结晶从水中获得结晶左旋葡聚糖。
• Detritylation of mono- and di-saccharide derivatives using ferric chloride hydrate
  作者：Xianglan Ding、Wei Wang、Fanzuo Kong

  DOI：10.1016/s0008-6215(97)00190-0

  日期：1997.10

  Quantitative detritylation of mono-and di-saccharide derivatives of diverse structure was achieved with FeCl3.6H(2)O in CH2Cl2 at room temperature. Benzyl, isopropylidene, isopropylthio, allyl, acetyl, and benzoyl O-protecting groups were not effected under the designated conditions. (C) 1997 Elsevier Science Ltd.