1-O-Acetyl-2,3,5-tri-O-benzoyl-α-D-arabinofuranose | 53403-35-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-Acetyl-2,3,5-tri-O-benzoyl-α-D-arabinofuranose
• 英文别名: (2R,3S,4R,5R)-2-Acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate；[(2R,3R,4S,5R)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 53403-35-3
• 化学式: C₂₈H₂₄O₉
• 分子量: 504.493
• InChiKey: GCZABPLTDYVJMP-DFIMXKNXSA-N

物化性质

• 沸点：
  621.0±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-Acetyl-2,3,5-tri-O-benzoyl-α-D-arabinofuranose 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 双(乙腈)氯化钯(II) 、 palladium on activated charcoal 、 Wilkinson's catalyst 吡啶 、 硫酸 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 140.5h， 生成
  参考文献：
  名称：

  An olefin cross metathesis approach to C-disaccharide analogs of the α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranoside motif found in the mycobacterial cell wall

  摘要：

  Reported is the synthesis of a C-disaccharide analog of the alpha-D-Araf-(1 -> 5)-alpha-D-Araf motif present in the cell wall of mycobacteria, including the human pathogen Mycobacterium tuberculosis. The key step is an olefin cross metathesis reaction that proceeds in excellent yield and which can be carried out on mmol scale. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.008
• 作为产物：
  描述：

  乙酸酐 、 methyl tri-O-benzoyl-α-D-arabinofuranoside 在 硫酸 作用下， 反应 1.0h， 以62.963%的产率得到
  参考文献：
  名称：

  银辅助金催化固相合成直链和支链寡糖

  摘要：

  与肽的固相合成不同，由于在进行糖苷化时面临固有的挑战，通过固相方法合成寡糖处于滞后状态。在这篇通讯中，发现银辅助金催化的糖苷化对于固相寡糖合成非常有效。催化条件下的糖苷化、与四当量供体的一次偶联、25°C 下不到 30 分钟的反应以及甲硅烷基和苯甲酸酯保护基团的树脂脱保护是其显着特征。光裂解聚糖具有受保护的氨基官能团，可用于生物共轭。该方法的多功能性是通过合成线性和支化呋喃五阿拉伯糖苷而建立的。

  DOI：

  10.1039/d1cc06270k

文献信息

• A Glycosylation Protocol Based on Activation of Glycosyl 2-Pyridyl Sulfones with Samarium Triflate
  作者：Grace X. Chang、Todd L. Lowary

  DOI：10.1021/ol005579k

  日期：2000.6.1

  [reaction--see text] Reaction of glycosyl 2-pridyl sulfones (e.g.,2) with alcohols and samarium(III) triflate affords glycosides in moderate to excellent yields. Benzylated sulfones can be activated in preference to their benzoylated counterparts, and the methodology has been used to prepare di- and trisaccharides containing both furanose and pyranose residues. Thioglycosides do not react under these

  [反应-见正文]糖基2-戊基砜（例如2）与醇和三氟甲磺酸sa的反应可得到中等至极好的糖苷收率。可以优先活化苯甲酰化的砜，而不是苯甲酰化的对应物，并且该方法已用于制备同时含有呋喃糖和吡喃糖残基的二糖和三糖。硫糖苷在这些条件下不反应，并且砜对通常用于活化硫糖苷的N-碘琥珀酰亚胺/三氟甲磺酸银助催化剂系统呈惰性。这种选择性允许通过正交糖基化方案有效地制备寡糖。
• A Chemo-Enzymatic Synthesis of β-d-Arabinofuranosyl Purine Nucleosides
  作者：Igor Mikhailopulo、Irina Konstantinova、Konstantin Antonov、Ilja Fateev、Anatoly Miroshnikov、Vladimir Stepchenko、Alexander Baranovsky

  DOI：10.1055/s-0030-1260010

  日期：2011.5

  β-d-arabinopyranose 1-phosphate in regard to PNP. Reaction of 2-fluoroadenine and α-d-arabinofuranose 1-phosphate is shifted towards the formation of Fludarabine, whereas the reaction of 2-amino-6-methoxypurine reached equilibrium at a ca. equimolar ratio of the base and Nelarabine. Recombinant E. coli uridine phosphorylase catalyzed the synthesis of 1-(β-d-arabinofuranosyl)thymine (ara-T) from thymine and

  使用α- d-阿拉伯呋喃糖1的9-（β- d-阿拉伯呋喃糖基）-2-氟腺嘌呤（氟达拉滨）和9-（β- d呋喃糖基）-2-氨基-6-甲氧嘌呤（去甲腺苷）的化学催化合成。描述了作为通用底物的β-磷酸酯和作为生物催化剂的重组大肠杆菌嘌呤核苷磷酸化酶（PNP）。麦克唐纳法被用来合成α - d-阿拉伯呋喃糖1-磷酸，它是与β- d-阿拉伯吡喃糖1-磷酸的混合物，从d的过酰基衍生物开始制备的。-不同异构体（异头）组成的阿拉伯糖。发现混合的磷酸盐可以成功地用于与PNP催化的嘌呤碱的反应，指出β- d-阿拉伯吡喃葡萄糖1-磷酸盐相对于PNP的惯性。2-氟腺嘌呤和α- d-呋喃糖1-磷酸的反应向氟达拉滨的方向转移，而2-氨基-6-甲氧基嘌呤的反应在约1小时达到平衡。碱和奈拉拉滨的等摩尔比。重组大肠杆菌尿苷磷酸化酶催化由胸腺嘧啶和α - d-阿拉伯呋喃糖1-磷酸合成1-（β- d-阿拉伯呋喃糖基）胸腺嘧啶（ara-T）。
• Compositions and methods for detecting and modulating rna activity and gene expression
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1418179A2

  公开（公告）日：2004-05-12

  Compositions and methods for modulating the activity of RNA and DNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. Reactive portions which act, alternatively, through phosphorodiester bond cleavage, through backbone sugar bond cleavage or through base modification are preferably employed. Groups which improve the pharmacodynamic and pharmacokinetic properties of the oligonucleotides are also useful in accordance with certain embodiments of this invention. Delivery of the reactive or non-reactive functionalities into the minor groove formed by the hybridization of the composition with the target RNA is also preferably accomplished. Therapeutics, diagnostics and research methods are also disclosed. Synthetic nucleosides and nucleoside fragments are also provided useful for elaboration of oligonucleotides and oligonucleotide analogs for such purposes.

  本文公开了调节 RNA 和 DNA 活性的组合物和方法。根据优选的实施方案，反义组合物由靶向部分和反应部分组成。反应部分最好通过磷酸二酯键裂解、骨架糖键裂解或碱基修饰起作用。根据本发明的某些实施方案，改善寡核苷酸药效学和药代动力学特性的基团也是有用的。最好还能将反应性或非反应性官能团输送到组合物与目标 RNA 杂交形成的次凹槽中。本发明还公开了治疗、诊断和研究方法。本发明还提供了合成核苷和核苷片段，可用于制备用于上述目的的寡核苷酸和寡核苷酸类似物。
• The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation
  作者：Polina I. Abronina、Ksenia G. Fedina、Nikita M. Podvalnyy、Alexander I. Zinin、Alexander O. Chizhov、Nikolay N. Kondakov、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2014.05.017

  日期：2014.9

  The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates.
• Farkas, Jiri; Fric, Ivo, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 6, p. 1291 - 1299
  作者：Farkas, Jiri、Fric, Ivo

  DOI：——

  日期：——