anti-(1S,2S)-dimethyl 1-chloro-2-hydroxypropanephosphonate | 1352401-34-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: anti-(1S,2S)-dimethyl 1-chloro-2-hydroxypropanephosphonate
• 英文别名: (1S,2S)-1-chloro-1-dimethoxyphosphorylpropan-2-ol
• CAS: 1352401-34-3
• 化学式: C₅H₁₂ClO₄P
• 分子量: 202.575
• InChiKey: IXWDAAZLQODWLH-CRCLSJGQSA-N

物化性质

• 沸点：
  268.9±30.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基溴硅烷 、 anti-(1S,2S)-dimethyl 1-chloro-2-hydroxypropanephosphonate 以 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

  摘要：

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.009
• 作为产物：
  描述：

  丙酮基膦酸二甲酯 在 磺酰氯 、 葡萄糖 作用下， 以 氯仿 为溶剂， 反应 1.08h， 生成 anti-(1S,2S)-dimethyl 1-chloro-2-hydroxypropanephosphonate
  参考文献：
  名称：

  Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

  摘要：

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.009

文献信息

• Asymmetric synthesis of (−)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step
  作者：Christian P. Marocco、Erik V. Davis、Julie E. Finnell、Phung-Hoang Nguyen、Scott C. Mateer、Ion Ghiviriga、Clifford W. Padgett、Brent D. Feske

  DOI：10.1016/j.tetasy.2011.10.009

  日期：2011.10

  Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.