[((2S,3R,4R,5S)-1-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester | 290834-62-7

• 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: [((2S,3R,4R,5S)-1-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester
• 英文别名: (2S,3R,4R,5S)-2-[[diethoxy(oxido)phosphaniumyl]-difluoromethyl]-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-1-prop-2-enylpyrrolidine
• CAS: 290834-62-7
• 化学式: C₃₄H₄₂F₂NO₆P
• 分子量: 629.681
• InChiKey: WTDYBCYCSCLCRI-YGXYGYJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [((2S,3R,4R,5S)-1-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 silica gel 、 sodium cyanoborohydride 、 magnesium sulfate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 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
• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 在 吡啶 、 甲基磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 [((2S,3R,4R,5S)-1-Allyl-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

文献信息

• Synthesis of new (difluoromethylphosphono)azadisaccharides designed as bisubstrate analogue inhibitors for GlcNAc:β-1,4 glycosyltransferases
  作者：Isabelle Gautier-Lefebvre、Jean-Bernard Behr、Georges Guillerm、Neil S Ryder

  DOI：10.1016/s0960-894x(00)00263-8

  日期：2000.7

  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.