phenyl 2,3,-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside | 905440-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bn(-4)]Glc(b)-SPh；[(2R,3R,4S,5R,6S)-5-benzoyloxy-2-(hydroxymethyl)-3-phenylmethoxy-6-phenylsulfanyloxan-4-yl] benzoate
• CAS: 905440-39-3
• 化学式: C₃₃H₃₀O₇S
• 分子量: 570.663
• InChiKey: VHJRZKUHOBNPFM-NGQWUPQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 caesium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 methyl phenyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucuronate
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z
• 作为产物：
  描述：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 吡啶 、 三乙基硅烷 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 phenyl 2,3,-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z

文献信息

• A highly efficient TEMPO mediated oxidation of sugar primary alcohols into uronic acids using 1-chloro-1,2-benziodoxol-3(1H)-one at room temperature
  作者：Varsha Tiwari、Vishnu Nayak Badavath、Adesh Kumar Singh、Jeyakumar Kandasamy

  DOI：10.1016/j.tetlet.2018.05.021

  日期：2018.6

  Oxidation of various sugar primary alcohols into corresponding uronic acids was demonstrated using 1-chloro-1,2-benziodoxol-3(1H)-one and TEMPO. The reaction proceeds at room temperature in good to excellent yields. Primary alcohols get oxidized selectively over the secondary alcohols under mild reaction conditions.

  使用1-氯-1,2-苯并恶恶唑3（1H）-one和TEMPO证明了各种糖伯醇被氧化为相应的糖醛酸。反应在室温下以良好至极好的收率进行。在温和的反应条件下，伯醇会比仲醇选择性地被氧化。
• 1,2-<i>trans</i> Glycosylation via Neighboring Group Participation of 2-<i>O</i>-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis
  作者：Milandip Karak、Yohei Joh、Masahiko Suenaga、Tohru Oishi、Kohei Torikai

  DOI：10.1021/acs.orglett.9b00220

  日期：2019.2.15

  The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol

  据报道，使用2- O-烷氧基甲基作为有效的立体定向取代基来构建1，2-反式糖苷键。观察到的立体选择性来自2- O-烷氧基甲基取代基和氧碳鎓离子之间的五元环状结构的分子内形成，这提供了预期的面部选择性。此外，观察到的立体控制和2 - O-烷氧基甲基保护的供体的极高反应性允许开发一锅顺序糖基化策略，该策略应成为组装寡糖的有力工具。
• A fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker as a safety-catch linker
  作者：Hiroshi Tanaka、Yosuke Tanimoto、Tetsuya Kawai、Takashi Takahashi

  DOI：10.1016/j.tet.2011.09.030

  日期：2011.12

  We report on the fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker. The phenyl ether linker is stable under both acidic and basic conditions but can be cleaved under mildly acidic conditions after reduction to a vinyl ether. The utility of the method was demonstrated by the synthesis of a trisaccharide. A protected trisaccharide with a light-fluorous tag was directly prepared

  我们报告了使用苯基醚接头的低聚氟辅助合成。苯基醚接头在酸性和碱性条件下均稳定，但在还原为乙烯基醚后可在弱酸性条件下裂解。通过三糖的合成证明了该方法的实用性。通过使用三个结构单元通过一锅糖基化直接制备具有轻氟标签的被保护的三糖，所述三个结构单元包含通过苯醚具有轻氟标签的结构单元。三糖的桦木还原提供了完全脱保护的三糖，该三糖具有通过乙烯基醚连接的氟标签，该糖很容易通过固相萃取进行纯化。通过用3％TFA的MeOH溶液处理，将标签从糖部分上切下。
• Simple Apparatus for Adding Small Amounts of Powder Materials under an Inert Atmosphere
  作者：Milandip Karak、Yohei Joh、Khamid U. Khodjaniyazov、Shamansur S. Sagdullaev、Tohru Oishi、Kohei Torikai

  DOI：10.1055/s-0039-1690689

  日期：2019.11

  addition of powder (solid) materials without contamination by air or moisture has been difficult, especially in the later stages of a reaction. Here, we offer a simple and small apparatus to realize powder addition with easy handling. Use of this apparatus permitted one-pot glycosylation reactions that required extremely dry conditions to be performed in a highly reproducible manner.

  在惰性气氛下添加反应物是合成化学中一项基本但极其重要的技术。尽管这在许多情况下可以通过使用手套箱或 Schlenk-and-syringe 技术来实现，但在没有空气或湿气污染的情况下直接添加粉末（固体）材料一直很困难，尤其是在反应的后期阶段。在这里，我们提供了一种简单而小巧的装置，可以轻松操作地实现粉末添加。使用该设备可以进行一锅糖基化反应，该反应需要以高度可重复的方式在极其干燥的条件下进行。
• Simple tool for adding solid catalysts without contamination by oxygen or moisture
  作者：Khamid U. Khodjaniyazov、Yohei Joh、Kohei Torikai

  DOI：10.1016/j.cattod.2021.06.006

  日期：2022.8