(1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptane-4,7-dione | 733769-96-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptane-4,7-dione
• CAS: 733769-96-5
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: ROBYCHJLCPHBQG-GGVZMXCHSA-N

物化性质

• 熔点：
  145 °C(Solv: methanol (67-56-1))
• 沸点：
  562.5±50.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptane-4,7-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到(αR,3R,4S)-3-(1-hydroxyethyl)-4-(hydroxymethyl)-1-(4-methoxyphenyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

  摘要：

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.034
• 作为产物：
  描述：

  (αR,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid 在 吡啶 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到(1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptane-4,7-dione
  参考文献：
  名称：

  Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

  摘要：

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.034

文献信息

• Synthesis of Enantiomerically Pure 2-Isoxacephems
  作者：Zsuzsanna S�nta、J�zsef Nagy、L�szl� P�rk�nyi、J�zsef Nyitrai

  DOI：10.1007/s00706-003-0135-9

  日期：2004.6.1

  (alphaR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted beta-lactams. The reduction of methyl [(alphaR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.
• Formation of 3-[1'-(dimethylphenylsilyl)ethyl]azetidin-2-ones: stereocontrolled formal approach to (.+-.)-thienamycin and (.+-.)-.beta.-(hydroxyalkyl)aspartic acid derivatives
  作者：Claudio Palomo、Jesus M. Aizpurua、Raquel Urchegui、Miren Iturburu

  DOI：10.1021/jo00031a044

  日期：1992.2

  Reaction between (+/-)-beta-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams, while addition of the Fleming's silylcuprate reagent to methyl crotonate and further enolate trapping by the above imines furnished the corresponding (+/-)-trans-3-[1'-(dimethylphenylsilyl)ethyl]-4-alkoxycarbonyl beta-lactams. These beta-lactams, upon appropriate chemical manipulations, provided a stereocontrolled route to (+/-)-thienamycin precursors and (+/-)-beta-(hydroxyalkyl)aspartic acid derivatives.