1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose | 28251-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose
• 英文别名: 3-O-p-toluenesulfonyl-1,2-O-isopropylidene-α-D-allofuranose；1,2-O-isopropylidene-3-O-toluenesulfonyl-α-D-allofuranose；1,2-O-isopropylidene-3-O-(p-tolylsulfonyl)allofuranose；1,2-O-Isopropyliden-3-O-tosyl-α-D-allofuranose；(3aR,5R,6R,6aR)-5-((R)-1,2-Dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate；[(3aR,5R,6R,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 28251-83-4
• 化学式: C₁₆H₂₂O₈S
• 分子量: 374.412
• InChiKey: YHCWPFMBKYICOM-KJWHEZOQSA-N

物化性质

• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 在 silica supported polyphosphoric acid 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以84%的产率得到1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose
  参考文献：
  名称：

  A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO₂

  摘要：

  Here, we report a highly selective, efficient and rapid method for the selective cleavage of primary acetonide using silica supported polyphosphoric acid (PPA-SiO2) for various carbohydrate substrates. Corresponding diols were obtained in good to excellent yields within 30 min using PPA-SiO2. Overall, PPA-SiO2 was found to be a useful catalyst for selective acetonide cleavage in carbohydrate substrates which may expand its utility in organic synthesis.

  DOI：

  10.1080/07328303.2019.1708374

文献信息

• C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
  作者：Adrienn Nagy、Barbara Csordás、Virág Zsoldos-Mády、István Pintér、Viktor Farkas、András Perczel

  DOI：10.1007/s00726-016-2346-5

  日期：2017.2

  d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–t X–Aaa– or –Aaa–t X–t X–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–c X–OH, producing longer

  为了获得用于制备同聚寡聚体或α/β-嵌合体肽的关键糖衍生物，正在开发经济和多克级的合成方法。尽管在文献中有描述，但3-氨基-3-脱氧-呋喃呋喃糖醛酸（H– t X– OH）及其C-3异构体立体异构体3-氨基-3-脱氧-呋喃呋喃糖醛酸的制备具有成本效益。此处描述了来自d-葡萄糖的（H– C X– OH）。阐述的本合成路线是（1）适用于大规模合成；（2）降低了试剂成本（例如降低了400倍）；（3）对于所有连续六个步骤（包括– t X –或– c X），优化后的产量约为80％或更高 –和（4）反应时间缩短。因此，一种新的合成路线一步工序的产量，成本，时间和纯化优化给出既为d -xylo和d -ribo氨基furanuronic氨基酸使用可持续化学（例如用有机溶剂较少色谱;使用连续-流动反应器）。我们的研究涵盖了必要的构建基块（例如– X –OMe，– X– O i Pr，– X –NHMe，Fmoc–
• Free-Radical Cyclizations onto Differently Substituted 1,2,3-Triazoles Installed in Sugar Templates
  作者：José Marco-Contelles、Mercedes Rodríguez-Fernández

  DOI：10.1021/jo001550i

  日期：2001.6.1

  The synthesis and manipulation of differently substituted 1,2,3-triazoles (7-11 and 12-16) installed in sugar templates gave compounds 29-34 and 44-50, after reaction with tributyltin hydride or tris(trimethylsilyl)silane. Following standard procedures compound 44 was transformed into piperidinose derivative 54. These compounds are chiral, useful building blocks for the synthesis of glycosidase inhibitors

  在与氢化三丁基锡或三（三甲基甲硅烷基）硅烷反应后，安装在糖模板中的不同取代的1,2,3-三唑（7-11和12-16）的合成和操作得到化合物29-34和44-50。按照标准方法，将化合物44转化为哌啶子糖衍生物54。这些化合物是手性的，有用的结构单元，用于合成稠合吡咯哌啶糖类型的糖苷酶抑制剂。
• A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO₂
  作者：Rahul R. Nikam、Kiran R. Gore

  DOI：10.1080/07328303.2019.1708374

  日期：2020.3.23

  Here, we report a highly selective, efficient and rapid method for the selective cleavage of primary acetonide using silica supported polyphosphoric acid (PPA-SiO2) for various carbohydrate substrates. Corresponding diols were obtained in good to excellent yields within 30 min using PPA-SiO2. Overall, PPA-SiO2 was found to be a useful catalyst for selective acetonide cleavage in carbohydrate substrates which may expand its utility in organic synthesis.
• Digitoxigenin 3-O-.beta.-D-furanosides
  作者：Ernest J. Prisbe、Julien P. H. Verheyden、Wayne W. Montgomery、Arthur M. Strosberg

  DOI：10.1021/jm00152a012

  日期：1986.2

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.