dimethyl (2-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamido)ethyl-1-d)phosphonate | 132155-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: dimethyl (2-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamido)ethyl-1-d)phosphonate
• CAS: 132155-74-9
• 化学式: C₁₄H₂₄NO₆P
• 分子量: 334.313
• InChiKey: RLVQOLOFXBGINZ-OJGXXKLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (S)-(-)-(2-Amino<1-D1>ethyl)phosphonsaeure 生成 dimethyl (2-((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamido)ethyl-1-d)phosphonate
  参考文献：
  名称：

  Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1988, p. 955 - 960

  摘要：

  DOI：

文献信息

• Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae
  作者：Friedrich Hammerschmidt、Hanspeter Kaehlig

  DOI：10.1021/jo00007a022

  日期：1991.3

  Nondeuteriated and deuteriated 2-(benzyloxy)ethanols (8a-c) were transformed into (2-hydroxyethyl)phosphonic acids (12a-c). 8c was prepared from dimethyl 2,3-O-isopropylidene-L-tartrate. 12b,c were fed to Streptomyces fradiae and were incorporated into fosfomycin (2), which was converted to amino phosphonic acid (-)-13. (-)-13 derived from 12b,c contained 42% and 34% deuterium, respectively. (1,2-Dihydroxyethyl)phosphonic acid ((+/-)-29) was not incorporated into fosfomycin. (S)- and (R)-(2-hydroxy[1-H-2-1]ethyl)phosphonic acids ((S)- and (R)-34) were prepared from (S)-2-(benzyloxy)[1-H-2-1]ethanol ((S)-30) and fed to S. fradiae. The deuterium of (R)-34 was lost, and the deuterium of (S)-34 was retained on incorporation into fosfomycin. The optical purity of (S)- and (R)-34 (84% and 86%, respectively) was determined by transformation to dimethyl ester and esterification with (+)-MTPA-Cl to afford 39b,c. 41 obtained from (S)-32 was identical with an authentic sample prepared from (S)-(2-amino[1-H-2-1]ethyl)phosphonic acid.