methyl 2,3,4-tri-O-benzyl-6-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranozyl)-α-D-mannopyranoside | 174741-70-9

• 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: methyl 2,3,4-tri-O-benzyl-6-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranozyl)-α-D-mannopyranoside
• 英文别名: Bz(-1)[Bz(-3)][Bz(-4)][Bz(-6)]Fruf(a2-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Man1Me；[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]oxolan-2-yl]methyl benzoate
• CAS: 174741-70-9
• 化学式: C₆₂H₅₈O₁₅
• 分子量: 1043.13
• InChiKey: QESSYFAXZXPMRQ-SUTOJSNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  77
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranozyl)-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以86%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-α-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：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 、 Ethyl 1,3,4,6-tetra-O-benzoyl-2-thio-D-fructofuranoside 在 DMTST 作用下， 以 乙腈 为溶剂， 以100%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(1,3,4,6-tetra-O-benzoyl-α-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

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.