2,3,4,6-tetra-O-benzyl-L-altrononolactam | 1309382-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-L-altrononolactam
• 英文别名: (3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-2-one
• CAS: 1309382-75-9
• 化学式: C₃₄H₃₅NO₅
• 分子量: 537.656
• InChiKey: ZXLUBBNCEANTCA-ZWDYZTTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactonamide 在 甲酸 、 乙酸酐 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2,3,4,6-tetra-O-benzyl-L-altrononolactam 、 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one
  参考文献：
  名称：

  Multi gram-scale synthesis of galactothionolactam and its transformation into a galactonoamidine

  摘要：

  We recently proposed to conduct selective glycosylation reactions after in situ activation of a glycosyl donor promoted by a transition metal complex immobilized in a macromolecular matrix. In order to develop this catalytic entity, a feasible multi gram-scale synthesis for 2,3,4,6-tetra-O-benzyl-D-galactothionolactam, its transformation into galactonoamidines with aromatic aglycon, and subsequent debenzylation conditions were developed. The potential for epimerization reactions at C-2 of the glycosidic ring during the transformations from the 2,3,4,6-tetra-O-benzyl-o-galactonolactam into the N-benzy1-2,3,4,6-tetra-O-benzyl-D-galactonoamidines via the 2,3,4,6-tetra-O-benzyl-D-galactothionolactam are discussed and additionally characterized by using density functional theory calculations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.021

文献信息

• Multi gram-scale synthesis of galactothionolactam and its transformation into a galactonoamidine
  作者：Rami Kanso、Susanne Striegler

  DOI：10.1016/j.carres.2011.02.021

  日期：2011.5

  We recently proposed to conduct selective glycosylation reactions after in situ activation of a glycosyl donor promoted by a transition metal complex immobilized in a macromolecular matrix. In order to develop this catalytic entity, a feasible multi gram-scale synthesis for 2,3,4,6-tetra-O-benzyl-D-galactothionolactam, its transformation into galactonoamidines with aromatic aglycon, and subsequent debenzylation conditions were developed. The potential for epimerization reactions at C-2 of the glycosidic ring during the transformations from the 2,3,4,6-tetra-O-benzyl-o-galactonolactam into the N-benzy1-2,3,4,6-tetra-O-benzyl-D-galactonoamidines via the 2,3,4,6-tetra-O-benzyl-D-galactothionolactam are discussed and additionally characterized by using density functional theory calculations. (C) 2011 Elsevier Ltd. All rights reserved.