ethyl tetra-O-benzyl-2-thio-α-D-fructofuranoside | 80763-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl tetra-O-benzyl-2-thio-α-D-fructofuranoside
• 英文别名: (2R,3S,4R,5R)-2-ethylsulfanyl-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolane
• CAS: 80763-70-8
• 化学式: C₃₆H₄₀O₅S
• 分子量: 584.777
• InChiKey: XUMNSJWSMTXMBS-PEDCNLCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-碘代丁二酰亚胺 、 ethyl tetra-O-benzyl-2-thio-α-D-fructofuranoside 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到(1,3,4,6-tetra-O-benzyl-D-fructofuranosyl)-N-succinimide
  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：

  Ethyl 1,3,4,6-tetra-O-benzoyl-2-thio-D-fructofuranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 ethyl tetra-O-benzyl-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

• Synthesis of <scp>d</scp>-Fructofuranosides Using Thioglycosides as Glycosyl Donors
  作者：Christian Krog-Jensen、Stefan Oscarson

  DOI：10.1021/jo951641t

  日期：1996.1.1

  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.