Phosphoric acid benzyl ester 2-bromo-ethyl ester (R)-2,3-dihydroxy-propyl ester | 156832-57-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: Phosphoric acid benzyl ester 2-bromo-ethyl ester (R)-2,3-dihydroxy-propyl ester
• 英文别名: benzyl 2-bromoethyl [(2R)-2,3-dihydroxypropyl] phosphate
• CAS: 156832-57-4
• 化学式: C₁₂H₁₈BrO₆P
• 分子量: 369.149
• InChiKey: KIPRFSUEHDQYGE-ZRIYNBNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phosphoric acid benzyl ester 2-bromo-ethyl ester (R)-2,3-dihydroxy-propyl ester 在 4-二甲氨基吡啶 、 甲酸 、 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-β-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：

  benzyl 2-bromoethyl (2,2-dimethyl-1,3-dioxolan-4-yl)methyl phosphate 在 磷酸 作用下， 以80%的产率得到Phosphoric acid benzyl ester 2-bromo-ethyl ester (R)-2,3-dihydroxy-propyl 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