2,3,5,6-tetra-O-benzoyl-β-D-galactofuranose | 108223-94-5

• 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: 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranose
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-hydroxyoxolan-2-yl]ethyl] benzoate
• CAS: 108223-94-5
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: VYILMYJVDLWSQH-KHSPHJBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranose 在 三氟甲磺酸三甲基硅酯 吡啶 、 MS 4 Angstroem 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-5,6-di-O-acetyl-1,2-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella

  摘要：

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00076-4
• 作为产物：
  描述：

  1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranose
  参考文献：
  名称：

  First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella

  摘要：

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00076-4

文献信息

• Selective removal of anomeric O-acetate groups in carbohydrates using HClO4–SiO2
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.tetlet.2006.03.050

  日期：2006.5

  A convenient methodology has been developed for the selective removal of the anomeric acyl group of carbohydrate derivatives using HClO4–SiO2 under acidic reaction conditions. Anomeric benzoyl groups can also be removed selectively following similar reaction conditions. The yields were excellent in all cases.

  已经开发了一种方便的方法，用于在酸性反应条件下使用HClO 4 -SiO 2选择性除去碳水化合物衍生物的异头酰基。在类似的反应条件下，也可以选择性地除去端基的苯甲酰基。在所有情况下，收率都非常好。
• Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors
  作者：Enrique A. Del Vigo、Carlos A. Stortz、Carla Marino

  DOI：10.1016/j.tet.2020.131719

  日期：2020.12

  The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowledge on this subject, we analyzed the relative reactivity of the OH-3 and OH-4 groups of 2,6-di-O-protected methyl α- and β-glucopyranosides in glycosylation

  糖基受体的不同羟基之间的区域选择性的知识对于规划寡糖合成的简单策略，最大限度地减少保护基的使用非常有价值。为了获得对该主题的更深入的了解，我们分析了2,6-di- O的OH-3和OH-4基团的相对反应性糖基化反应中保护的甲基α-和β-吡喃葡萄糖苷。通过简单的程序制备糖基受体，并将半乳糖-吡喃糖基和呋喃糖基三氯乙酰亚氨酸酯评估为糖基供体。将实验结果与通过分子建模方法获得的结果进行对比。分子模型和实验结果基本吻合。已经表明，通过选择正确的端基异构体和保护基团，可以使用适当的葡糖基受体选择性地安装1→3或1→4键。
• 6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity
  作者：Jeane Vaugenot、Abderrafek El Harras、Olivier Tasseau、Rémi Marchal、Laurent Legentil、Boris Le Guennic、Thierry Benvegnu、Vincent Ferrières

  DOI：10.1039/c9ob02596k

  日期：——

  Standard glycosylation of unprotected 6-fluorogalactofuranoside turned to three competitive reactions and afforded difuranosides able to impact growth of Leishmania tarentolae.

  不保护的6-氟半乳糖苷的标准糖基化转化为三个竞争反应，并得到能够影响蜥蜴利什曼原虫生长的二氧杂环糖苷。
• Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions
  作者：Anup Kumar Misra、Geetanjali Agnihotri

  DOI：10.1016/j.carres.2003.12.020

  日期：2004.3

  A metal-free, mild, efficient and chemoselective hydrolysis of several thioalkylglycosides (1) into their corresponding 1-hydroxy sugars (2) using sodium N-chloro-p-toluenesulfonamide trihydrate (chloramine-T) without affecting other functional groups is reported. (C) 2004 Published by Elsevier Ltd.
• Facile synthesis of benzyl β-d-galactofuranoside. A convenient intermediate for the synthesis of d-galactofuranose-containing molecules
  作者：Karina Mariño、Luciana Baldoni、Carla Marino

  DOI：10.1016/j.carres.2006.06.004

  日期：2006.9

  Benzyl beta-D-galactofurano side was efficiently obtained from 1,2,3,5,6-penta-O-benzoyl-alpha, beta-D-galactofuranose, via benzyl 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranoside. Conditions for the O-debenzylation were investigated in order to evaluate the synthetic application of the benzyl group as an anomeric protector of a galactofuranose moiety in synthetic strategies involving galactofuranose. (c) 2006 Elsevier Ltd. All rights reserved.