(3S,4R)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(prop-2-enyl)-2-azetidinone | 151908-05-3

• 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)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(prop-2-enyl)-2-azetidinone
• 英文别名: (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-(prop-2-enyl)-2-azetidinone；(3S,4R)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-prop-2-enylazetidin-2-one
• CAS: 151908-05-3
• 化学式: C₂₀H₄₁NO₂Si₂
• 分子量: 383.722
• InChiKey: YBJZSRVEKUZPPP-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(prop-2-enyl)-2-azetidinone 在 氧气 、 臭氧 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (3S,4R)-4-(3,3-dibromoprop-2-enyl)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c
• 作为产物：
  描述：

  (3S^*,4R^*)-4-allyl-1-tert-butyldimethylsilyl-3-(1,2-dihydroxy-2-propyl)-2-azetidinone 在 咪唑 、 sodium periodate 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(prop-2-enyl)-2-azetidinone
  参考文献：
  名称：

  碳青霉烯和青霉烯抗生素。IV。（5R *，6S *）-6-[（（R *）-1-羟乙基] -2-官能化的甲基碳青霉烯和青霉烯衍生物的合成和抗菌活性。

  摘要：

  合成了R enantiomer的2-乙酰氧基甲基和2-(杂环芳香)硫甲基的碳青霉烯和青霉素抗生素，这些化合物在C-6位上具有1-(R*)-羟基乙基侧链（6, 7, 8，以及45, 59, 47, 49, 51），并测定了它们的抗菌活性。

  DOI：

  10.1248/cpb.33.4382

文献信息

• A new strategy for the synthesis of carbapenems. A formal total synthesis of (+)-thienamycin.
  作者：Gregg B. Feigelson

  DOI：10.1016/s0040-4039(00)74078-0

  日期：1993.7

  A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin serves to demonstrate this strategy.

  提出了形成碳青霉烯环系统的新方法。关键步骤涉及路易斯酸介导的β-内酰胺氮与合适放置的侧链的α-酮酯的环缩合。噻吩霉素合成中已知的关键中间体的制备可证明这一策略。
• Synthesis of 3-alkoxycarbonyl-1β-methylcarbapenem using palladium-catalyzed amidation of vinyl halide
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1016/s0040-4039(01)02091-3

  日期：2002.1

  3-Alkoxycarbonyl-1β-methylcarbapenem could be synthesized using a palladium-catalyzed CN bond-forming reaction. In this reaction, the use of Pd(OAc)2 and DPEphos gave a good result, and generation of Pd(0) in the absence of a base is necessary to increase the yield.

  可以通过钯催化的C bondN键形成反应合成3-烷氧羰基-1β-甲基咔啉。在该反应中，使用Pd（OAc）2和DPEphos可获得良好的结果，并且在不存在碱的情况下生成Pd（0）对于提高产率是必需的。
• Synthesis of 3-Alkoxycarbonyl-1β-methylcarbapenem by Using the Palladium-Catalyzed C−N Bond-Forming Reaction between Vinyl Halide and β-Lactam Nitrogen
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1021/jo020584i

  日期：2003.4.1

  3-Alkoxycarbonyl-1beta-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and beta-lactam nitrogen. In this reaction, the use of Pd(OAc)(2) and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)(2) in the absence of a base is necessary to increase the yield.
• Carbapenem and penem antibiotics. IV. Synthesis and antibacterial activity of (5R*,6S*)-6-((R*)-1-hydroxyethyl)-2-functionalized-methyl carbapenem and penem derivatives.
  作者：HISAO ONA、SHOICHIRO UYEO、TAKASHI FUKAO、MASAYOSHI DOI、TADASHI YOSHIDA

  DOI：10.1248/cpb.33.4382

  日期：——

  Racemic 2-acetoxymethyl and 2-(heteroaromatic) thiomethyl carbapenem and penem antibiotics having a 1-(R*)-hydroxyethyl side-chain at C-6 (6, 7, 8, and 45, 59, 47, 49, 51) were synthesized, and their antibacterial activities were determined.

  合成了R enantiomer的2-乙酰氧基甲基和2-(杂环芳香)硫甲基的碳青霉烯和青霉素抗生素，这些化合物在C-6位上具有1-(R*)-羟基乙基侧链（6, 7, 8，以及45, 59, 47, 49, 51），并测定了它们的抗菌活性。
• Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1021/jo030123c

  日期：2003.10.1

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).