(3R,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-methoxyazetidin-2-one | 119171-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-methoxyazetidin-2-one
• 英文别名: (3R,4R)-3-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-4-methoxyazetidin-2-one；4R-methoxy-3S-[1'R-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one；(3R,4R)-3-[(1R)-1-{[tert-Butyl(dimethyl)silyl]-oxy}ethyl]-4-methoxyazetidin-2-one；(3R,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methoxyazetidin-2-one
• CAS: 119171-36-7
• 化学式: C₁₂H₂₅NO₃Si
• 分子量: 259.421
• InChiKey: WRYGZMZEDYVKSY-WCABBAIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-methoxyazetidin-2-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  An Unprecedented Cleavage of the .beta.-Lactam Ring: Stereoselective Synthesis of Chiral .beta.-Amido Cyanides

  摘要：

  A new method has been developed for the synthesis of chiral beta-amido cyanides by means of the regioselective cleavage of beta-lactams in the presence of a TMSOTf catalyst and RCN.

  DOI：

  10.1021/jo00084a002
• 作为产物：
  描述：

  4R-methoxy-3S-[1'R-(tert-butyldimethylsilyloxy)ethyl]-1-(1'R-phenylethyl)azetidin-2-one 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(3R,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-methoxyazetidin-2-one
  参考文献：
  名称：

  Diastereoselective construction of azetidin-2-ones by electrochemical intramolecular C–C bond forming reaction

  摘要：

  A convenient: method for synthesis of optically active azetidin-2-ones using electrochemical oxidation has been exploited. The method consists of a diastereoselective intramolecular C-C bond forming reaction between active methylene and methyne groups through an electrochemical system in which positive iodine species acted as mediators under mild conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.087

文献信息

• (2R,3R)-3-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl Acetate in Zinc- and Samarium-Promoted Substitution Reactions with Methyl 2-Bromopropanoate and Methyl (2-Bromomethyl)prop-2-enoate. Unusual Cleavage of the N1‒C4 Bond in Azetidin-2-one Derivative with Migration of Methoxycarbonyl Group in Synthetic Approaches to Carbapenems and Their Analogs
  作者：Z. R. Valiullina、L. S. Khasanova、N. K. Selezneva、L. V. Spirikhin、Yu. N. Belokon’、M. S. Miftakhov

  DOI：10.1134/s1070428018070096

  日期：2018.7

  l(dimethyl) silyl]oxy}ethyl]-1-(2-methoxy-2-oxoethyl)-4-oxoazetidin-2-yl}-2(RS)-methyl-3-oxopentanoate which underwent fragmentation through cleavage of the N1–C4 bond under the action of sodium bis(trimethylsilyl)-amide in THF at–78°C. The resulting acyclic amide, dimethyl (2R,S,3Z)-2-[(1R)-1-[tert-butyl(dimethyl)-silyl]oxy}ethyl)]-4-methyl-5-oxohept-3-enoylamino}malonate, was smoothly converted

  锌在（2 R，3 R）-3-[（1 R）-1-[叔丁基（二甲基）甲硅烷基]氧基}-乙基] -4-氧杂ze啶-2-基的Barbier型反应中的使用具有卤素衍生物的乙酸乙烯酯导致形成预期的取代产物。标题化合物与由sa粉，催化量的碘和2-溴丙酸甲酯在THF中制备的试剂反应，得到异常取代产物2-（2 S，3 S）-3-[（1 R）-1-[[叔丁基（二甲基）甲硅烷基]氧基}乙基] -4-氧杂氮杂环丁烷-2-基} -2（R，S）-3-氧戊酸甲酯 后者与溴乙酸甲酯烷基化，得到2-（2 S，3 S）-3-[（1 R）-1-[叔丁基（二甲基）甲硅烷基]氧基}乙基] -1-（2-甲基）甲氧基-2-氧乙基）-4-氧杂氮杂环丁烷-2-基} -2（RS）-3-氧戊酸甲酯，在双（三甲基甲硅烷基）-酰胺钠的作用下，通过裂解N 1 -C 4键进行裂解在–78°C下的THF中。生成的无环酰胺二甲基（2 R，S，3
• A Novel Method for the Alkoxylation of Azetidin-2-ones at the 4-Position.
  作者：Yasuyiki KITA、Norio SHIBATA、Naoki YOSHIDA、Takashi TOHJO

  DOI：10.1248/cpb.40.1044

  日期：——

  4-Sulfinylazetidin-2-ones were reacted with various types of tributyltin alkoxides in the presence of a catalytic amount of trimethylsilyltrifluoromethanesulfonate to give the corresponding trans-alkoxyazetidin-2-ones in high yields.

  在一定量的三甲基硅基三氟甲磺酸盐催化下，4-亚磺酰基氮杂环丁烷-2-酮与各种类型的三丁基锡烷氧基化合物发生反应，以高产率得到相应的反式烷氧基氮杂环丁烷-2-酮。
• Kita, Yasuyuki; Shibata, Norio; Kawano, Noriyuki, Journal of the Chemical Society. Perkin transactions I, 1996, # 18, p. 2321 - 2329
  作者：Kita, Yasuyuki、Shibata, Norio、Kawano, Noriyuki、Yoshida, Naoki、Matsumoto, Keita、Takebe, Yasushi

  DOI：——

  日期：——
• Diastereoselective construction of azetidin-2-ones by electrochemical intramolecular C–C bond forming reaction
  作者：Daishirou Minato、Satoshi Mizuta、Masami Kuriyama、Yoshihiro Matsumura、Osamu Onomura

  DOI：10.1016/j.tet.2009.09.087

  日期：2009.11

  A convenient: method for synthesis of optically active azetidin-2-ones using electrochemical oxidation has been exploited. The method consists of a diastereoselective intramolecular C-C bond forming reaction between active methylene and methyne groups through an electrochemical system in which positive iodine species acted as mediators under mild conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• An Unprecedented Cleavage of the .beta.-Lactam Ring: Stereoselective Synthesis of Chiral .beta.-Amido Cyanides
  作者：Yasuyuki Kita、Norio Shibata、Naoki Yoshida、Noriyuki Kawano、Keita Matsumoto

  DOI：10.1021/jo00084a002

  日期：1994.3

  A new method has been developed for the synthesis of chiral beta-amido cyanides by means of the regioselective cleavage of beta-lactams in the presence of a TMSOTf catalyst and RCN.