n-octyl D-galactofuranoside | 202403-49-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-octyl D-galactofuranoside
• 英文别名: octyl D-galactofuranoside；(2S,3R,4R)-2-[(1R)-1,2-dihydroxyethyl]-5-octoxyoxolane-3,4-diol
• CAS: 202403-49-4
• 化学式: C₁₄H₂₈O₆
• 分子量: 292.373
• InChiKey: VZLNXIZRQPJOEU-LSGALXMHSA-N

物化性质

• 熔点：
  95-97°C
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-octyl D-galactofuranoside 在 吡啶 、 硫酸 、 三氟化硼乙醚 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-1-((2S,3S,4R,5S)-3,4-diacetoxy-5-(4-nitrophenoxy)tetrahydrofuran-2-yl)ethane-1,2-diyl diacetate
  参考文献：
  名称：

  An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

  摘要：

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.016
• 作为产物：
  描述：

  辛醇 、 D-(+)-galactose 在 三氯化铁 、 calcium chloride 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到n-octyl D-galactofuranoside
  参考文献：
  名称：

  An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

  摘要：

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.016

文献信息

• Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions
  作者：Vincent Ferrières、Jérôme Joutel、Rachel Boulch、Myriam Roussel、Loı̈c Toupet、Daniel Plusquellec

  DOI：10.1016/s0040-4039(00)00887-x

  日期：2000.7

  Sulfinyl β-d-galactofuranosides 3(R,S) and 9(R,S) were used as new hexofuranosyl donors in glycosylation reactions. Activation by trifluoromethanesulfonic anhydride involved different reaction pathways depending on the stereochemistry at the sulfur atom. Experimental results underlined a more suitable reactivity of 3(R) and 9(R) versus 3(S) and 9(S), respectively, for the synthesis of β-d-galactofuranosides

  亚磺酰基β-d-半乳糖呋喃糖苷3（R，S）和9（R，S）被用作糖基化反应中的新的呋喃呋喃糖基供体。三氟甲磺酸酐的活化涉及不同的反应途径，这取决于硫原子的立体化学。实验结果强调了3（R）和9（R）分别比3（S）和9（S）更适合用于合成β-d-半乳糖呋喃糖苷。
• A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY
  作者：Vincent Ferrières、Myriam Roussel、Muriel Gelin、Daniel Plusquellec

  DOI：10.1081/car-100108662

  日期：2001.12.31

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.
• An efficient route to per-O-acetylated hexofuranoses
  作者：Vincent Ferrières、Muriel Gelin、Rachel Boulch、Loı̈c Toupet、Daniel Plusquellec

  DOI：10.1016/s0008-6215(98)00290-0

  日期：1998.12

  Anomeric mixtures of per-O-acetylated D-galacto-, D-gluco- and D-manno-furanose derivatives were prepared via the corresponding n-octyl hexofuranosides under mild acetolysis conditions. The crystal X-ray data of 1,2,3,5,6-penta-O-acetyl-alpha-D-mannofuranose corroborate the proposed structures. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase
  作者：Caroline Rémond、Richard Plantier-Royon、Nathalie Aubry、Michael J. O’Donohue

  DOI：10.1016/j.carres.2005.01.016

  日期：2005.3

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.