1-O-allyl-6-O-trityl-β-D-glucopyranoside | 225376-17-0

• 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-O-allyl-6-O-trityl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-prop-2-enoxy-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 225376-17-0
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: SMNUMGQSKFVLET-IURCNINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-allyl-6-O-trityl-β-D-glucopyranoside 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 三苯基膦 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 115.5h， 生成 (2R,3R,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-8-trimethylsilanyl-oct-6-yn-1-ol
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i
• 作为产物：
  描述：

  可得然胶 在 吡啶 、 乙酰氯 作用下， 生成 1-O-allyl-6-O-trityl-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] β-1,6-GLUCAN CETUXIMAB ANTIBODY CONJUGATES
  [FR] CONJUGUÉS DE Β-1,6-GLUCANE ET DE L'ANTICORPS CÉTUXIMAB

  摘要：

  本发明涵盖了将Cetuximab或相关的Cetuximab抗体与β-1,6-葡聚糖寡聚体结合的实施例。因此，本发明包括将Cetuximab与一个或多个β-1,6-葡聚糖寡聚体结合的组合物，以及制备和/或使用这样的β-1,6-葡聚糖结合物的方法等。在某些实施例中，本发明的β-1,6-葡聚糖结合物可用作治疗或治疗方法中的治疗剂。

  公开号：

  WO2016196682A1

文献信息

• Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells
  作者：Melanie Reiß、Andreas Brietzke、Thomas Eickner、Florian Stein、Alexander Villinger、Christian Vogel、Udo Kragl、Stefan Jopp

  DOI：10.1039/d0ra01370f

  日期：——

  investigation we chose α- and β-methyl-, β-allyl- and β-phenyl D-glucopyranose as well as four 1-deoxy-pentoses. In order to be able to classify the results, more ionic liquids with different structural motives were examined for cytotoxicity. Here, we present data that confirm the biocompatibility of such ILs consisting of naturally occurring molecules or their derivatives. The synthesized carbohydrate

  大量天然存在的碳水化合物及其手性和结构的多样性导致了对基于碳水化合物的 IL 进行系统研究的想法。为此，我们研究了不同醚基（主要是甲基或乙基醚）对仲 OH 基团的影响，以及不同构型对物理性质（如熔点、热稳定性，尤其是对细胞毒性的影响）的影响。在本次调查中，我们选择了 α-和 β-甲基-、β-烯丙基-和 β-苯基D-吡喃葡萄糖以及四种 1-脱氧戊糖。为了能够对结果进行分类，检查了更多具有不同结构动机的离子液体的细胞毒性。在这里，我们提供的数据证实了这种由天然分子或其衍生物组成的 ILs 的生物相容性。测试了合成的基于碳水化合物的 ILs 作为药物洗脱球囊等医疗应用涂层添加剂的适用性。
• Probing myo-inositol 1-phosphate synthase with multisubstrate adducts
  作者：Rania M. Deranieh、Miriam L. Greenberg、Pierre-B. Le Calvez、Maura C. Mooney、Marie E. Migaud

  DOI：10.1039/c2ob26577j

  日期：——

  The synthesis of a series of carbohydrate–nucleotide hybrids, designed to be multisubstrate adducts mimicking myo-inositol 1-phosphate synthase first oxidative transition state, is reported. Their ability to inhibit the synthase has been assessed and results have been rationalised computationally to estimate their likely binding mode.

  报道了一系列碳水化合物-核苷酸杂交物的合成，这些杂交物被设计为多底物加合物，旨在模拟肌醇-1-磷酸合酶的首次氧化过渡态。评估了它们抑制合酶的能力，并通过计算方法对结果进行了合理化，以估计它们可能的结合模式。
• A Practical Synthetic Method for a- and b-Glycosyloxyacetic Acids
  作者：Tadakatsu Mandai、Hiroshi Okumoto、Tetsuta Oshitari、Katsuyoshi Nakanishi、Katsuhiko Mikuni、Ko-ji Hara、Ko-zo Hara

  DOI：10.3987/com-99-s43

  日期：——

  Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into alpha- and beta-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.
• Diastereoselective bromination of allyl glycosides using tetrabutylammonium tribromide
  作者：Giuseppe Bellucci、Cinzia Chiappe、Felicia D'Andrea

  DOI：10.1016/0957-4166(94)00378-o

  日期：1995.1

  Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60% have been obtained by diastereoselective addition of Bq to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or Cd using tetrabutylammonium tribromide, followed by hydrolysis. The absolute configuration is shown to depend on the position of the free hydroxyl and on the configuration at the anomeric centre.