N-[(2S,3R,4R,5S,6R)-2-Allyloxy-5-hydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide | 205987-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-Allyloxy-5-hydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS: 205987-15-1
• 化学式: C₁₉H₂₇NO₇
• 分子量: 381.426
• InChiKey: UIAZCUNWHUPCKP-NNIGNNQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  106.48
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-2-Allyloxy-5-hydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide 、 2,3,4-tris-O-(phenylmethyl)-β-L-fucopyranosyl fluoride 在 4 A molecular sieve 、 lithium perchlorate 、 cesium fluoride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以99%的产率得到N-[(2S,3R,4R,5S,6R)-2-Allyloxy-4-(4-methoxy-benzyloxy)-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-((3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis of Fucosyl Saccharides under Neutral Conditions in Solutions of Lithium Perchlorate in Dichloromethane

  摘要：

  Trisaccharides embodying the Fuc-alpha-(1-2)-Gal or the Fuc-alpha-(1-2)-Glc substructure can be built up under neutral conditions by glycosylation of selectively deprotected glycosyl acceptor disaccharides with 2,3,4-tri-O-benzyl fucosyl fluoride in 0.07 M solutions of LiClO4 in CH2Cl2. The glycosyl and the galactosyl trisaccharides, which are stereoisomers of the carbohydrate determinant of the human blood group H, are obtained in high yield and with complete alpha-selectivity. The glycosyl acceptor disaccharides with a deblocked 2-OH group in the saccharide unit are obtained by treatment of the respective 1,2-anhydro carbohydrates with glycosyl acceptors in 0.07 M LiClO4/CH2Cl2.

  DOI：

  10.1002/(sici)1521-3765(19980310)4:3<494::aid-chem494>3.0.co;2-8
• 作为产物：
  描述：

  allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 barium dihydroxide 、 camphor-10-sulfonic acid 、 barium(II) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 200.0h， 生成 N-[(2S,3R,4R,5S,6R)-2-Allyloxy-5-hydroxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis of Fucosyl Saccharides under Neutral Conditions in Solutions of Lithium Perchlorate in Dichloromethane

  摘要：

  Trisaccharides embodying the Fuc-alpha-(1-2)-Gal or the Fuc-alpha-(1-2)-Glc substructure can be built up under neutral conditions by glycosylation of selectively deprotected glycosyl acceptor disaccharides with 2,3,4-tri-O-benzyl fucosyl fluoride in 0.07 M solutions of LiClO4 in CH2Cl2. The glycosyl and the galactosyl trisaccharides, which are stereoisomers of the carbohydrate determinant of the human blood group H, are obtained in high yield and with complete alpha-selectivity. The glycosyl acceptor disaccharides with a deblocked 2-OH group in the saccharide unit are obtained by treatment of the respective 1,2-anhydro carbohydrates with glycosyl acceptors in 0.07 M LiClO4/CH2Cl2.

  DOI：

  10.1002/(sici)1521-3765(19980310)4:3<494::aid-chem494>3.0.co;2-8