1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-α,β-galactofuranose | 275358-18-4

• 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-2,3,4,6-tetra-O-benzoyl-α,β-galactofuranose
• 英文别名: 1-O-acetyl-2,3,5,6-tetra-O-benzoyl-D-galactofuranose；2,3,5,6-tetra-O-benzoyl-D-galactofuranosyl acetate；1-O-acetyl-2,3,5,6-tetra-O-benzoylgalactofuranose
• CAS: 275358-18-4
• 化学式: C₃₆H₃₀O₁₁
• 分子量: 638.628
• InChiKey: DHKYMCKGIPKWAT-AZDDEXEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-α,β-galactofuranose 在 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 20.0h， 生成 Dibenzyl 2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl phosphate
  参考文献：
  名称：

  The first chemical synthesis of UDP-α-D-galactofuranose

  摘要：

  尿苷5'-二磷酸α-D-半乳糖呋喃糖，可能是自然界中D-半乳糖呋喃糖残基的生物化学供体，由α-D-半乳糖呋喃糖磷酸和尿苷5'-单磷酸合成。

  DOI：

  10.1039/b000210k
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 硫酸 、 三氯化铁 作用下， 以 吡啶 为溶剂， 生成 1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-α,β-galactofuranose
  参考文献：
  名称：

  Improved Chemical Synthesis of UDP-Galactofuranose

  摘要：

  [GRAPHICS]A reliable and efficient synthetic route to UDP-alpha -D-galactofuranose (UDP-Galf) has been developed. Reaction of UMP-N-methylimidazolide with Galf 1-phosphate proceeds rapidly to provide UDP-Galf with excellent reproducibility and in a yield approximately twice as high as those reported previously.

  DOI：

  10.1021/ol016170d

文献信息

• Synthesis and biological properties of galactofuranosyl-containing fluorescent dyes
  作者：Laurent Legentil、Sorya Belaz、Jean-Pierre Gangneux、Florence Robert-Gangneux、Vincent Ferrières

  DOI：10.1016/j.bmcl.2016.11.090

  日期：2017.1

  fluorescent galactofuranosides were synthesized and their biological activities evaluated on non-infected and Leishmania infected macrophages. Both tagged scaffolds were able to penetrate macrophages. Compared to the activity of the parent octyl galactofuranoside used as a reference, the fluorescein-conjugate showed altered biological properties while the rhodamine 6G one synergistically acted with the

  合成了两种荧光半乳糖呋喃糖苷，并对未感染和利什曼原虫感染的巨噬细胞评估了它们的生物学活性。两个标记的支架都能够穿透巨噬细胞。与作为参考的母体辛基半乳糖呋喃糖苷的活性相比，荧光素结合物显示出改变的生物学特性，而若丹明6G与脂质链协同作用以显着增加抗寄生虫活性。
• The First Chemical Synthesis of UDP[6-3H]-α-D-galactofuranose
  作者：Karina Mariño、Carla Marino、Carlos Lima、Luciana Baldoni、Rosa M. de Lederkremer

  DOI：10.1002/ejoc.200500056

  日期：2005.7

  hampered by the lack of a labeled galactofuranose nucleotide. In the present work we describe the chemical synthesis of UDP-α-D-[6-3H]Galf and we prove its effectiveness for incorporation of radioactive galactofuranose into a natural acceptor. This is the first report on the chemical synthesis of a labeled donor of galactofuranose with the potential for studying the galactofuranosyltransferases independently

  呋喃半乳糖代谢是开发用于治疗某些微生物感染的新型化学治疗剂的良好靶点。这是一个有效的目标，因为哺乳动物中不存在呋喃半乳糖。两种酶参与含有呋喃半乳糖的分子的生物合成：变位酶，催化 UDP-Galp 和 UDP-Galf 的相互转化，以及 D-呋喃半乳糖基转移酶。目前正在研究变位酶的作用机制及其抑制作用，而对呋喃半乳糖基转移酶的研究因缺乏标记的呋喃半乳糖核苷酸而受到阻碍。在目前的工作中，我们描述了 UDP-α-D-[6-3H]Galf 的化学合成，并证明了其将放射性呋喃半乳糖掺入天然受体的有效性。这是关于呋喃半乳糖标记供体的化学合成的第一份报告，具有独立于 UDP-Galp 变位酶研究呋喃半乳糖转移酶的潜力。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1016/j.carres.2013.03.032

  日期：2013.6

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747
  作者：Yan Qiao、Buko Lindner、Ulrich Zähringer、Peter Truog、Richard R. Schmidt

  DOI：10.1016/j.bmc.2010.04.006

  日期：2010.6.1

  The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a beta-D-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-O to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-O hydrolytically labile D-alanyl residues. As typical LTA for this array of compounds LTA 1a was synthesized. To this end, from D-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-O-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and deprotection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four D-alanyl residues led after global deprotection and purification to target molecule 1a possessing on average about two D-alanyl residues at 2-O of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material. (C) 2010 Published by Elsevier Ltd.