ethyl 2-thio-α-D-fructofuranoside | 80763-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-thio-α-D-fructofuranoside
• 英文别名: Ethyl 2-thio-alpha-d-fructofuranoside；(2R,3S,4S,5R)-2-ethylsulfanyl-2,5-bis(hydroxymethyl)oxolane-3,4-diol
• CAS: 80763-60-6
• 化学式: C₈H₁₆O₅S
• 分子量: 224.278
• InChiKey: LWWCVEKTXLPUFS-OOJXKGFFSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  463.2±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.46
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.15
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-thio-α-D-fructofuranoside 在 sodium hydride 、 DMTST 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(1,3,4,6-tetra-O-benzyl-β-D-fructofuranozyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of d-Fructofuranosides Using Thioglycosides as Glycosyl Donors

  摘要：

  Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate accepters. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3 .-etherate-promoted reaction gave the benzoylated ethyl 2-thio-alpha,beta-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested accepters, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only alpha-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave alpha/beta-mixtures.

  DOI：

  10.1021/jo951641t
• 作为产物：
  描述：

  1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.5h， 生成 ethyl 2-thio-α-D-fructofuranoside
  参考文献：
  名称：

  Synthesis of d-Fructofuranosides Using Thioglycosides as Glycosyl Donors

  摘要：

  Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate accepters. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3 .-etherate-promoted reaction gave the benzoylated ethyl 2-thio-alpha,beta-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested accepters, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only alpha-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave alpha/beta-mixtures.

  DOI：

  10.1021/jo951641t

文献信息

• Iterative Synthesis of Inulin-Type Fructooligosaccharides Enabled by Stereoselective β-<scp>d</scp>-Fructofuranosylation
  作者：Liang-Jing Zou、Xing Yang、Xi-Rui Zhao、Huan He、Dan Zhang、Hao Song、Fei Xue、Yong Qin

  DOI：10.1021/acs.joc.2c01849

  日期：2022.11.18

  iterative synthesis of five inulin-type FOSs with degrees of polymerization ranging from 3 to 7 via highly stereoselective β-(2 → 1)-d-fructofuranosylation on a gram scale. Central to the synthesis is the decisive use of the 1-O-TIPS-6-O-picoloyl-protected fructofuranosyl thioglycoside donor, which assured the excellent β-selective glycosylation by the hydrogen-bond-mediated aglycone delivery (HAD).

  菊粉型低聚果糖 (FOS) 构成了丰富的具有重要生物活性的果聚糖亚群。然而，获得具有准确结构的高纯度和高质量的低聚果糖仍然具有挑战性。我们在此报道了通过高度立体选择性 β-(2 → 1) -d-呋喃果糖基化在克尺度上首次迭代合成聚合度为 3 到 7 的五种菊糖型 FOS 。合成的核心是决定性地使用 1- O -TIPS-6- O -picoloyl-protected fructofuranOSyl thioglycOSide 供体，这通过氢键介导的糖苷配基递送 (HAD) 确保了出色的 β-选择性糖基化。