({(2S,3R,4R,5S)-1-[2-((2S,3S,4S,5R,6S)-5-Acetylamino-4-hydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-ethyl]-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl}-difluoro-methyl)-phosphonic acid diethyl ester | 290834-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ({(2S,3R,4R,5S)-1-[2-((2S,3S,4S,5R,6S)-5-Acetylamino-4-hydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-ethyl]-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl}-difluoro-methyl)-phosphonic acid diethyl ester
• CAS: 290834-66-1
• 化学式: C₄₂H₅₈F₂N₃O₁₁P
• 分子量: 849.907
• InChiKey: QVBFGTROUUGAOQ-WNKKZLESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  59.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  166.51
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  ({(2S,3R,4R,5S)-1-[2-((2S,3S,4S,5R,6S)-5-Acetylamino-4-hydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-ethyl]-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl}-difluoro-methyl)-phosphonic acid diethyl ester 在 palladium on activated charcoal 甲酸铵 作用下， 以 乙醇 为溶剂， 生成 N-[(2S,3R,4S,5S,6S)-5-[2-[(2S,3R,4R,5S)-2-[diethoxyphosphoryl(difluoro)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-yl]ethylamino]-4-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Synthesis of new (difluoromethylphosphono)azadisaccharides designed as bisubstrate analogue inhibitors for GlcNAc:β-1,4 glycosyltransferases

  摘要：

  We report here the design, synthesis and antifungal evaluation of a new model of bisubstrate analogue inhibitor for glycosyltransferases. The synthetic strategy relies on the reductive amination between the aldehyde derived from an N-allylphosphono-pyrrolidine and an aminosugar. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00263-8
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (3R,4S,5S,6S)-3-acetylamino-5-amino-2-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 在 sodium methylate 、 sodium cyanoborohydride 、 magnesium sulfate 、 乙酰氯 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 ({(2S,3R,4R,5S)-1-[2-((2S,3S,4S,5R,6S)-5-Acetylamino-4-hydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-ethyl]-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl}-difluoro-methyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of new (difluoromethylphosphono)azadisaccharides designed as bisubstrate analogue inhibitors for GlcNAc:β-1,4 glycosyltransferases

  摘要：

  We report here the design, synthesis and antifungal evaluation of a new model of bisubstrate analogue inhibitor for glycosyltransferases. The synthetic strategy relies on the reductive amination between the aldehyde derived from an N-allylphosphono-pyrrolidine and an aminosugar. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00263-8