CAS: 24138-28-1; (2S,5R,6S)-6-Bromo-3,3-Dimethyl-7-Oxo-4-Thia-1-Azabicyclo[3.2.0]Heptane-2-Carboxylic Acid

该化合物是一种双环化合物,具有硫化碘环状结构,该化合物的特点是存在一个溴原子,一个碳酸性功能组和一个可促进其再活动及潜在生物活动的氯酮组;2S,5R,6S)配置显示的立体化学学结构显示其子组的具体空间安排,可对其药用特性产生重大影响;该化合物的独特结构可能使其与生物目标发生相互作用,使其对药用化学具有兴趣;此外,多种功能组的存在表明存在各种化学反应的可能性,包括酯化和核糖替代.

结构式图片

MSDS等安全信息

上下游产品

6-Aminopenicillanic Acid 6-aminopenicillanic acid 6,6-dibromopenicillanic acid 6-aminopenicillanic acid Benzyl 6α-bromopenicillanate brobactam penicillanic acid diphenylmethyl 6α-bromopenicillanate

合成工艺路线路线简述

  • 合成目标产物 [2S-(2Alpha,5Alpha,6Alpha)]-6-Bromo-3,3-Dimethyl-7-Oxo-4-Thia-1-Azabicyclo[3.2.0]Heptane-2-Carboxylic Acid 主要起始原料 (2S,5R,6S)-6-Amino-3,3-Dimethyl-7-Oxo-4-Thia-1-Azabicyclo[3.2.0]Heptane-2-Carboxylic Acid
  • (文献来源)合成步骤主要原料 (2S,5R,6S)-6-Amino-3,3-Dimethyl-7-Oxo-4-Thia-1-Azabicyclo[3.2.0]Heptane-2-Carboxylic Acid
📜6-Aminopenicillanic Acid置于硫酸,Sodium Bromide,Sodium Nitrite体系中,用 甲醇,水 用作溶剂,化学反应 0.5H,以72%的收率获得[2S-(2Alpha,5Alpha,6Alpha)]-6-溴-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸
参考文献:关于6β-溴openicillanic酸抑制β-内酰胺酶的化学反应
标题:关于6β-溴openicillanic酸抑制β-内酰胺酶的化学反应
摘要:来自蜡样芽孢杆菌的强大的β-内酰胺酶i抑制剂6β-溴去甲硅酸与酶中的丝氨酸残基反应,并通过酯键与二氢噻嗪(2A)结合.给出了该任务的光谱和化学证据,并将证据与从相关模型二氢噻嗪(2B)获得的证据进行了比较.在某些条件下,结合物种经历了由自氧化反应引起的进一步化学变化.模型二氢噻嗪(2B)经历了类似的自氧化反应.
Doi:10.1039/p19800002322

海关参考信息

专利信息


专利号:US-4383949-A
优先权日:1980-07-16
标题:Preparation of 3-bromo-4-fluorobenzaldehyde and its acetals
发明人:MAURER FRITZ; RIEBEL HANS-JOCHEM; PRIESNITZ UWE; KLAUKE ERICH
权利人:BAYER AG
摘要:A process for the preparation of a 3-bromo-4-fluorobenzaldehyde acetal of the formula ##STR1## in which R 1 is methyl or ethyl, n which comprises reacting a 3-bromo-4-fluoro-benzoic acid halide with ammonia to form 3-bromo-4-fluoro-benzoic acid amide, dehydrating said amide to form 3-bromo-4-fluoro-benzonitrile, reacting the nitrile with formic acid in the presence of a catalyst at a temperature between about 0° and 150° C. to form 3-bromo-4-fluorobenzaldehyde, and reacting said aldehyde with R 1 OH or a derivative thereof capable of forming an acetal. The amide and nitrile are new compounds. The acetals are known intermediates in the synthesis of pyrethroid-like insecticides.

专利号:US-4283531-A
优先权日:1978-06-02
标 题:Synthesis of β-lactams having a substituted hydroxymethylene group at the position α to the lactam carbonyl group
发明人:GANGULY ASHIT K; GIRIJAVALLABHAN VIYYOOR M; CAVENDER PATRICIA; SARRE OLGA; MCCOMBIE STUART W
权利人:SCHERING CORP
摘要:β-Lactams having a substituted hydroxymethylene group at the position α to the lactam carbonyl group are prepared by reaction of an α-halo-β-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone. n Also described are novel penicillins and cephalosporins having useful antibacterial activity.

专利号:US-4468351-A
优先权日:1983-06-06
标题 :Process for debromination of dibromopenicillanic acid and derivatives
发明人:PIRIE DONALD K; WEEKS PAUL D
权利人:PFIZER
摘要:A process for the debromination of 6-monobromo- and 6,6-dibromopenicillanic acid, and various derivatives thereof, by the action of a bisulfite salt. The debrominated compounds produced find various utilities, as beta-lactamase inhibitors useful in therapy in combination with known beta-lactam antibiotics, or as intermediates in the further synthesis of useful beta-lactam compounds.

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Synthesis Of (5R)-(Z)-6-(1-Methyl-1,2,3-Triazol-4-Ylmethylene)Penem-3-Carboxylic Acid, A Potent Broad Spectrum β-Lactamase Inhibitor, From 6-Aminopenicillanic Acid
作者:Neal F. Osborne,Richard J. Atkins,Nigel J. P. Broom,Steven Coulton,John B. Harbridge,Michael A. Harris,Irene Stirling-François,Graham Walker
摘要:(5R)-(Z)-6-(1-Methyl-1,2,3-Triazol-4-Ylmethylene)Penem-3-Carboxylic Acid 34 (Brl 42715) Has Been Prepared From 6-Aminopenicillanic Acid 4 (6-Apa) By A Short, Stereoselective And Efficient Route Via The Novel Intermediate. P-Methoxybenzyl (5R,6S)-6-Bromopenem-3-Carboxylate 17.Elaboration Of 6-Apa 4 To The Azetidinone Disulfide 10 By Established Methodology, Followed By Reductive Formylation Provided The Crystalline C-4 Formylthio-Azetidinone Derivative 29. Cyclization Of The Oxalimide 28, Obtained By Ozonolysis Of The Formylthio Derivative 29. To The Crystalline 6 Alpha-Bromopenem Ester 17 Was Effected By Way Of The Phosphite-Mediated Carbonyl-Carbonyl Coupling Reaction.

合成参考文献

参考DOI号:10.1055/s-2004-837299
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