(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carboxymethyl-2-azetidinone | 88669-70-9

• 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: (3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carboxymethyl-2-azetidinone
• 英文别名: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one；(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidine；2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]acetic acid
• CAS: 88669-70-9
• 化学式: C₁₃H₂₅NO₄Si
• 分子量: 287.431
• InChiKey: IPVISRLWWJZCAD-FXPVBKGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carboxymethyl-2-azetidinone 在 盐酸 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 水 为溶剂， 反应 1.92h， 生成 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
  参考文献：
  名称：

  .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

  摘要：

  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.

  DOI：

  10.1021/jo00041a032
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 palladium on activated charcoal 、 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 (3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carboxymethyl-2-azetidinone
  参考文献：
  名称：

  通过新的三烷氧基磷烷-硫酯的分子内Wittig反应有效合成碳青霉烯

  摘要：

  通过草酰亚胺9与亚磷酸三烷基酯反应获得的新的三烷氧基磷杂环戊烷硫醇酯10通过分子内Wittig反应有效地环化，得到碳青霉烯11。

  DOI：

  10.1016/s0040-4039(01)81292-2

文献信息

• An efficient carbapenem synthesis via an intramolecular Wittig reaction of new trialkoxyphosphorane-thiolesters
  作者：Akira Yoshida、Yawara Tajima、Noriko Takeda、Sadao Oida

  DOI：10.1016/s0040-4039(01)81292-2

  日期：——

  New trialkoxyphosphorane-thiolesters 10, obtained by reaction of oxalimides 9 with trialkyl phosphite, were efficiently cyclized by an intramolecular Wittig reaction to give carbapenems 11.

  通过草酰亚胺9与亚磷酸三烷基酯反应获得的新的三烷氧基磷杂环戊烷硫醇酯10通过分子内Wittig反应有效地环化，得到碳青霉烯11。
• Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate
  作者：Yoshio Ito、Yuko Kobayashi、Takeo Kawabata、Mitsuru Takase、Shiro Terashima

  DOI：10.1016/s0040-4020(01)89105-5

  日期：1989.1

  Two types of the carbapenem key intermediates (4 and 6) have been efficiently synthesized from inexpensive (S)-ethyl lactate (7). Thus, (S)-2-benzyloxypropanal readily obtainable from 7 was condensed with di-p-anisylmethylamine to give the chiral imine. The [2+2]-cycloaddition reaction of diketene with the imine underwent in a highly stereoselective manner, yielding the desired 3,4-trans-3-acetyl-β-lactam

  两种类型的碳青霉烯关键中间体（4和6）是由廉价的（S）-乳酸乙酯（7）有效合成的。因此，将容易从7得到的（S）-2-苄氧基丙醛与二对茴香基甲胺缩合，得到手性亚胺。双烯酮与亚胺的[2 + 2]-环加成反应以高度立体选择性的方式进行，产生了所需的3,4-trans-3-乙酰基-β-内酰胺（13a）作为主要产物（非对映选择性为7-10： 1）。这分别以9个步骤和6个步骤进行了详细说明，分别为4和6。
• Structure-activity relationships in the 2-arylcarbapenem series. Synthesis of 1-methyl-2-arylcarbapenems
  作者：Ravindra Nath Guthikonda、L. D. Cama、M. Quesada、M. F. Woods、T. N. Salzmann、B. G. Christensen

  DOI：10.1021/jm00388a022

  日期：1987.5

  tert-butyldimethylsilyl esters of the azetidinones 6-8b served as the crucial synthons in the preparation of the potentially useful ylide pyridyl thio esters 18-20. These intermediates were utilized to synthesize a host of title carbapenems 25-30d, 32, and 49-53. The antimicrobial properties and DHP-I susceptibility of these carbapenems were studied with reference to thienamycin.

  氮杂环丁酮6-8b的不稳定的叔丁基二甲基甲硅烷基酯在制备潜在有用的内酯吡啶基硫代硫酯18-20中起关键的合成子作用。这些中间体被用来合成许多标题碳青霉烯25-30d，32和49-53。参照噻菌霉素研究了这些碳青霉烯类的抗菌特性和DHP-1敏感性。
• Stereocontrolled synthesis of (+)-thienamycin from 3(R)-hydroxybutyric acid
  作者：Takamasa Iimori、Masakatsu Shibasaki

  DOI：10.1016/s0040-4039(00)98542-3

  日期：——

  The vinyloxyborane(5), prepared from (+)--phenyl-3()-butanethioate, 9-BBN triflate and diisopropylethylamine, reacted with -(3-benzyloxypropylidene)benzylamine to give the β-benzylamino thiol ester(6) in a moderate yield, which was efficiently converted to the optically pure thienamycin intermediate(10).

  所述vinyloxyborane（5）中，从（+）制备-苯基-3-（）-butanethioate，9-BBN三氟甲磺酸酯和二异丙基乙胺，用反应- （3- benzyloxypropylidene）苄胺，得到β -苄基氨基硫羟酸酯（6 a）中的产量适中，可有效转化为光学纯的硫霉素中间体（10）。
• The asymmetric synthesis of β-lactam antibiotics - IV. A formal synthesis of thienamycin.
  作者：David A. Evans、Eric B. Sjogren

  DOI：10.1016/s0040-4039(00)85107-2

  日期：1986.1

  Oxidative cleavage of crotonate imide aldol adduct 6b provides the configurationally stable aldehyde 4. Transformation of this aldehyde to enantiomerically pure β-lactams is described.

  巴豆酸酰亚胺醛醇醛加合物6b的氧化裂解提供了构型稳定的醛4。描述了该醛向对映体纯的β-内酰胺的转化。