1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose | 37074-90-1

• 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 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-β-D-glucopyranose；6-Trityl-1,2,3,4-tetra-O-acetyl-beta-D-glucose；[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 37074-90-1
• 化学式: C₃₃H₃₄O₁₀
• 分子量: 590.627
• InChiKey: GTJGUFOLNHYRQE-HXBJCGEWSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  0.180 °C(Press: 0.0008 Torr)
• 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-trityl-β-D-glucopyranose 在 triphenylmethyl perchlorate 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-葡萄糖
  参考文献：
  名称：

  Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters

  摘要：

  DOI：

  10.1016/s0008-6215(00)84672-8
• 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-trityl-β-D-glucopyranose
  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

• Preparation of some (1→6)-linked disaccharides, and their derivatives suitable for protein modification
  作者：Reiko T. Lee、Yuan C. Lee

  DOI：10.1016/s0008-6215(00)80793-4

  日期：1982.2

  Abstract Synthetic methods for the preparation of per- O -acetylated, (1→6)-linked disaccharides containing either a d -galactose or a d -glucose residue at the reducing end are described. In these methods, 1,2,3,4-tetra- O -acetyl-6- O -trityl-β- d -glucopyranose was first converted into 1,2,3,4-tetra- O -acetyl-β- d -glucopyranose ( 1 ) by rapid treatment with 90% trifluoroacetic acid, followed by

  摘要描述了合成在还原端含有ad-半乳糖或ad-葡萄糖残基的过氧乙酰化（1→6）连接的二糖的合成方法。在这些方法中，首先将1,2,3,4-四-O-乙酰基-6-O-三苯甲基-β-d-吡喃葡萄糖转化为1,2,3,4-四-O-乙酰基-β-d -吡喃葡萄糖（1），先用90％三氟乙酸快速处理，然后进行快速分离，以最大程度地减少O-酰基迁移。通过将1或1,2：3,4-二-O-异亚丙基-d-吡喃半乳糖与过-O-乙酰基糖基卤化物糖基化形成二糖。如果存在，则除去所得二糖中的异亚丙基，并将二糖过-O-乙酰化。过-O-乙酰化的β-Gal-（1→6）-Glc和β-GlcNAc-（1→6）-Gal 从而得到过-O-乙酰化的α-Gal-（1→6）-Gal和β-Gal-（1→6）-Gal的混合物（比例为3：7）。通过先前报道的反应顺序，将过-O-乙酰化的Gal-（1→6）-Gal二糖转化为（2,2-二甲氧基乙基）氨基羰基
• Synthèses de 6-O-β-d-apiofuranosyl-β-d-glucopyranosides de monoterpényle
  作者：Oubadjim Mbaïraroua、Thang Ton-That、Claude Tapiéro

  DOI：10.1016/0008-6215(94)80057-x

  日期：1994.2

  benzyl and 2-phenylethyl as aglycon moiety were prepared using the stereospecific trichloroacetimidate Schmidt method. The key intermediate diholoside 1,2,3,4-tetra-O-acetyl-6-O-[(3-C-acetoxymethyl)-2,3-di-O-acetyl-β- d -erythrofuranosyl)-β- d -glucopyranose was obtained by Kochetkov glycosylation of a branched-chain tetrofuranose cyanoethylidene derivative. The NMR data (1H and 13C) of the synthetic compounds

  摘要具有（S）-3,7-二甲基-1,6-辛二烯-3-基（芳樟基）的合成apiosyl-glucosides；（R）-1-甲基-1-（4-甲基-3-环己烯-1-基）乙基（松油酰基）；（E）和（Z）-3,7-二甲基-2,6-辛二烯-1-基（香叶基和神经基）；（S）-3,7-二甲基-6-辛烯-1-基（香茅基）；使用立体特异性三氯乙酰亚胺酸酯Schmidt方法制备了作为糖苷配基的苄基和2-苯乙基。关键中间体二乙醇苷1,2,3,4-四-O-乙酰基-6-O-[（3-C-乙酰氧基甲基）-2,3-二-O-乙酰基-β-d-呋喃呋喃糖基）-β- d-吡喃葡萄糖是通过科奇特科夫对支链的四呋喃糖氰基亚乙基衍生物进行糖基化而获得的。报道了合成化合物的NMR数据（1H和13C）和apiose部分的糖基化位移。
• SUGAR CONTAINING, AMPHIPHILIC COPOLYMERS
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20160120984A1

  公开（公告）日：2016-05-05

  Disclosed herein are polymers made from at least one monomer of formulae (I), (II), (III), and (IV), in combination with a monomer of formula (V) that may be used in pharmaceutical formulations. These polymers comprise a hydrocarbon backbone and are made from monomers that contain at least one carbon-carbon double bond. Methods of making these polymers are also disclosed.

  本文揭示了由公式(I)、(II)、(III)和(IV)中至少一种单体与公式(V)中的一种单体结合而制成的聚合物，可用于制备药物配方。这些聚合物包括一个碳氢骨架，由含有至少一个碳-碳双键的单体制成。同时还揭示了制备这些聚合物的方法。
• Selective deprotection of trityl group on carbohydrate by microflow reaction inhibiting migration of acetyl group
  作者：Atsushi Miyagawa、Ryusuke Tomita、Kenta Kurimoto、Hatsuo Yamamura

  DOI：10.1080/00397911.2016.1156703

  日期：2016.3.18

  ABSTRACT The trityl group is an important and useful protecting group for primary hydroxy groups on carbohydrates. However, during deprotection, neighboring acetyl groups can easily migrate to the deprotected hydroxy groups. Hence, deprotection of trityl groups was optimized using a microreactor with regard to flow rate, reagent concentration, reaction time, and substrate concentration. The optimized

  摘要 三苯甲基是碳水化合物上伯羟基的重要且有用的保护基团。然而，在脱保护过程中，相邻的乙酰基很容易迁移到脱保护的羟基上。因此，使用微反应器在流速、试剂浓度、反应时间和底物浓度方面优化三苯甲基的脱保护。优化的微流反应条件抑制了迁移，可应用于大规模反应和其他底物。图形概要
• Degradable polymer and process for production thereof
  申请人：Matsumoto Akikazu

  公开号：US20090069448A1

  公开（公告）日：2009-03-12

  In one embodiment of the present invention, a degradable polymer having a peroxide bond therein is disclosed. The degradable polymer can be utilized in the fields of medicals or medical materials, can be applied to a DDS or gene delivery system, and can be used as a novel polymeric material or environmentally-friendly material. A polyperoxide, which is an alternating copolymer, has in a side chain thereof, a functional group (which is a substituent comprising a therapeutic molecule), a water-soluble substituent, or a biodegradable substituent.

  在本发明的一个实施例中，揭示了具有过氧化物键的可降解聚合物。这种可降解聚合物可以应用于医学领域或医疗材料领域，可以用于DDS或基因传递系统，并可用作新型聚合材料或环保材料。一种聚过氧化物，即交替共聚物，在其侧链中具有一个功能基团（该基团包括治疗分子）、水溶性基团或可生物降解基团。