rac-3-<1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-acetoxyazetidin-2-one | 78963-48-1

• 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: rac-3-<1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-acetoxyazetidin-2-one
• 英文别名: dl-(3R*,4R*)-4-acetoxy-3-<(1R*)-(tert-butyldimethylsiloxy)ethyl>azetidin-2-one；dl-(3R*,4R*)-4-acetoxy-3-<(1S*)-(tert-butyldimethylsiloxy)ethyl>azetidin-2-one；dl-(3R*,4R*)-4-acetoxy-3-[(1S*)-(tert-butyldimethylsiloxy)ethyl]azetidin-2-one；[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate
• CAS: 78963-48-1
• 化学式: C₁₃H₂₅NO₄Si
• 分子量: 287.431
• InChiKey: GWHDKFODLYVMQG-UISBYWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-3-<1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-acetoxyazetidin-2-one 生成
  参考文献：
  名称：

  PRASAD, J. SIVA;LIEBESKIND, LANNY S., TETRAHEDRON LETT., 29,(1988) N 34, C. 4257-4260

  摘要：

  DOI：
• 作为产物：
  描述：

  <3S-<3α(S^*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-acetyl-2-azetidinone 以93%的产率得到
  参考文献：
  名称：

  ITO, YOSHIO;KOBAYASHI, YUKO;KAWABATA, TAKEO;TAKASE, MITSURU;TERASHIMA, SH+, TETRAHEDRON, 45,(1989) N8, C. 5767-5790

  摘要：

  DOI：

文献信息

• A practical synthesis of a key intermediate for the production of β-lactam antibiotics
  作者：Gianfranco Cainelli、Paola Galletti、Daria Giacomini

  DOI：10.1016/s0040-4039(98)01700-6

  日期：1998.10

  exahydro-1,3,5-triazine in presence of a Lewis acid and (R)-3-(t-butyldimethylsilyloxy)butyric acid chloride with Et3N directly furnish (3S,1′R)-N-p-methoxyphenyl-3-(1-t-butyldimethylsilyloxy)ethylazetidin-2-one with good diastereo-selectivity. This product is transformed into the 4-acetoxy-azetidinone 1, a key intermediate in the synthesis of β-lactam antibiotics.

  N-（对甲氧基苯基）-六氢-1,3,5-三嗪在路易斯酸和（R）-3-（叔丁基二甲基甲硅烷氧基）丁酰氯与Et 3 N的存在下直接提供（3 S，1' [R ）- ñ - p -甲氧基苯基-3-（1-吨-butyldimethylsilyloxy）乙基氮杂-2-酮与良好非对映选择性。该产物被转化为4-乙酰氧基-氮杂环丁酮1，这是合成β-内酰胺类抗生素的关键中间体。
• From penicillin to penem and carbapenem. VII. Synthesis and antibacterial activity of penem derivatives.
  作者：KATSUMI FUJIMOTO、YUJI IWANO、KOICHI HIRAI、SHINICHI SUGAWARA

  DOI：10.1248/cpb.34.999

  日期：——

  The azetidinone derivative (6), which has an (R)-hydroxyethyl substituent at the C-3 position, was prepared efficiently from 6-aminopenicillanic acid. From the dibromo seco derivative (10), compounds of the same type (16 and 17), but in dl-form, were obtained. Compounds 6 and 16 were reacted with various thiocarboxylic acids to obtain the penem derivatives (23a-n).The minimum inhibitory concentration values of these penems against various microorganisms were, determined, and the structure-activity relationship is discussed.

  由6-氨基青霉烷酸有效地制备了在C-3位具有(R)-羟乙基取代基的氮杂环丁酮衍生物(6)。由二溴仲衍生物(10)，得到相同类型的化合物(16和17)，但为dl-形式。化合物6和16与各种硫代羧酸反应得到青霉烯类衍生物(23a-n)。测定了这些青霉烯类衍生物对各种微生物的最低抑菌浓度值，并讨论了其构效关系。
• 一种培南类药物中间体的非对映异构体的合成方法
  申请人：浙江工业大学

  公开号：CN114773378A

  公开（公告）日：2022-07-22

  本发明公开了一种培南类药物中间体的非对映异构体的合成方法，本发明合成的化合物(3S，4S)‑3‑[(R)‑1‑叔丁基二甲基硅氧乙基]‑4‑乙酰氧基‑2‑氮杂环丁酮是培南类药物的关键中间体4AA的非对映异构体，对建立4AA的检测方法，分析4AA的含量，并控制4AA生产中的杂质限度具有重要意义，为4AA的质量控制提供了重要保障；
• .beta.-Lactams. 2. Diastereoselective alkylative discrimination of racemic 3-substituted 4-acetoxyazetidin-2-ones and its application to the synthesis of a chiral key intermediate for carbapenem syntheses
  作者：Yoshimitsu Nagao、Yunosuke Nagase、Toshio Kumagai、Yasuhiro Kuramoto、Shigeaki Kobayashi、Yoshinori Inoue、Tooru Taga、Hirokazu Ikeda

  DOI：10.1021/jo00041a032

  日期：1992.7

  Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42%, 20%, and 9% yields, respectively, after chromatographic purification. Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45%, 29%, and 5% yields, respectively. Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems. Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.
• Yoshida, Akira; Hayashi, Teruo; Takeda, Noriko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2899 - 2909
  作者：Yoshida, Akira、Hayashi, Teruo、Takeda, Noriko、Oida, Sadao、Ohki, Eiji

  DOI：——

  日期：——