Phosphorochloridic acid 2-bromo-ethyl ester (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 169684-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphorochloridic acid 2-bromo-ethyl ester (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: (4R)-4-[[2-bromoethoxy(chloro)phosphoryl]oxymethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 169684-98-4
• 化学式: C₈H₁₅BrClO₅P
• 分子量: 337.535
• InChiKey: PALQKILFPVTKDL-MSSWUJIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Phosphorochloridic acid 2-bromo-ethyl ester (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 在 4-二甲氨基吡啶 、 甲酸 、 磷酸 、 三氟化硼乙醚 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-2-O-palmitoyl-3-O-<(2-bromoethoxy)benzoxyphosphoryl>glycerol
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043
• 作为产物：
  描述：

  2-溴乙基二氯膦酸酯 、 (S)-(+)-1,2-异亚丙基甘油 在 N-甲基吗啉 作用下， 生成 Phosphorochloridic acid 2-bromo-ethyl ester (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of (2R)- and (2S)-.beta.-D-Glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol: A New Antifungal Phosphocholine

  摘要：

  The discovery of a new of antifungal agent, a glycosylated phosphatidylcholine, is reported, and the syntheses of the first two members of this series, (2S)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol and (2R)-beta-D-glucopyranos-1-yl-2-O-palmitoyl-3-O-phosphatidylcholinylglycerol, are described. Their activities against the pathogenic fungi Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus are also reported.

  DOI：

  10.1021/jo00128a043