2,3,5-tri-O-acetyl-D-arabinofuranose | 64609-15-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-acetyl-D-arabinofuranose
• 英文别名: [(2R,3R,4S)-3,4-diacetyloxy-5-hydroxyoxolan-2-yl]methyl acetate
• CAS: 64609-15-0
• 化学式: C₁₁H₁₆O₈
• 分子量: 276.243
• InChiKey: RCDVSNGCFMKYLB-NFLHVTIKSA-N

物化性质

• 沸点：
  361.0±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-D-arabinofuranose 在 N-碘代丁二酰亚胺 、 硫酸 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 methyl 2,3,5-tri-O-acetyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Conversion of Pyranose Glycals to Furanose Derivatives:  A New Route to Oligofuranosides

  摘要：

  Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetyl-galactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform C-13 enrichment.

  DOI：

  10.1021/jo9815406
• 作为产物：
  描述：

  methyl 2,3,5-tri-O-acetyl-D-arabinofuranoside 在 硫酸 、 三丁基锡乙氧化物 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 2,3,5-tri-O-acetyl-D-arabinofuranose
  参考文献：
  名称：

  化学酶法合成阿拉伯甘露聚糖（AM）糖缀合物作为结核病的潜在疫苗。

  摘要：

  导致结核病（TB）的分枝杆菌感染是2018年全球死亡的十大主要死因之一，脂质阿拉伯甘露聚糖（LAM）已被证实是TB细胞表面最重要的抗原多糖。在这项研究中，已经开发了一种方便的合成方法，用于合成三种衍生自LAM的支链低聚糖，其中通过流化酶水解制备核心构件，收率很高。经过数个糖基化步骤后，将获得的寡糖与重组人血清白蛋白（rHSA）和离体抗体偶联为了评估糖结合产物对人LAM抗体的亲和力，使用了从数名受TB感染的患者那里获得的血清进行ELISA测试。评价结果是肯定的，尤其是化合物21表现出优异的活性，可以被认为是未来针对结核病的新的糖缀合物疫苗研发的先导化合物。

  DOI：

  10.1016/j.ejmech.2020.112578

文献信息

• A Concise Synthesis of Oligosaccharides Derived From Lipoarabinomannan (LAM) with Glycosyl Donors Having a Nonparticipating Group at C2
  作者：Zhihao Li、Changping Zheng、Marco Terreni、Teodora Bavaro、Matthieu Sollogoub、Yongmin Zhang

  DOI：10.1002/ejoc.201901915

  日期：2020.4.16

  is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach has been developed for the synthesis of oligosaccharides derived from LAM starting with commercially available substrates and reagents. The key steps for stereoselective construction of glycosidic bonds by

  导致结核病 (TB) 的分枝杆菌感染是全球十大主要死亡原因之一，而脂阿拉伯甘露聚糖 (LAM) 已被证实在此过程中发挥着重要作用。在这项研究中，开发了一种方便的合成方法，用于从市售底物和试剂开始合成源自 LAM 的寡糖。实现了在没有相邻参与组的情况下通过与供体糖基化的受体立体选择性构建糖苷键的关键步骤。值得注意的是，采用酶水解制备甘露糖结构单元，并采用桦木反应一步法脱去乙酰基和苄基以及还原叠氮基，避免了多次化学过程。最后，
• Synthesis and antitumor activity of new shikonin glycosides
  作者：Yehua Su、Jiansheng Xie、Yanguang Wang、Xun Hu、Xianfu Lin

  DOI：10.1016/j.ejmech.2010.02.002

  日期：2010.7

  Eleven shikonin glycosides were synthesized and evaluated for their antitumor activity in vitro. Some of them were found to exhibit cytotoxic activities against both drug sensitive cell lines (K562, MCF-7 and HL60) and their drug resistant cell sublines (K562/ADR, MCF-7/ADR and HL60/ADR). (C) 2010 Published by Elsevier Masson SAS.
• A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction
  作者：Shun Kitahata、Akira Katsuyama、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.0c00665

  日期：2020.4.3

  A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the alpha-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.
• Synthesis of Oligosaccharides of Motifs D and E of Arabinogalactan Present in <i>Mycobacterium </i><i>t</i><i>uberculosis</i>
  作者：Mukund K. Gurjar、L. Krishnakanth Reddy、Srinivas Hotha

  DOI：10.1021/jo010180a

  日期：2001.6.1

  Syntheses of the ethyl glycosides of 5-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose and 5-O-(alpha -D-arabinofuranosyl)-6-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.
• Synthesis of 4′,8-dihydroxyisoflavon-7-yl α-d-arabinofuranoside
  作者：Masao Shiozaki

  DOI：10.1016/s0957-4166(99)00135-4

  日期：1999.4

  4',8-Dihydroxyisoflavon-7-yl alpha-D-arabinofuranoside 1 (A-76202), which is a strong alpha-glucosidase I and II inhibitor, was synthesized by the glycosylation of 2,3,5-tri-O-benzyl-alpha-D-arabinofuranosyl bromide 2 and the lithium salt of 4',8-diallyloxy-7-hydroxyisoflavone 4, and successive deprotection of allyl groups and benzoyl esters of the glycosylated product 5. (C) 1999 Elsevier Science Ltd. All rights reserved.