CAS: 53558-93-3; (R)-5-Oxotetrahydrofuran-2-Carboxylicacid

该化合物是一种带有碳酸性功能组的手性γ-内酯衍生物,使它成为有机合成和制药应用的多用途中间体.它的立体特性(R)配置对于非对称合成特别有用,能够生产对等纯化合物.化合物的内酯和碳酸乙烯摩尔底酸为进一步衍生提供了反应场所,如酯化或恐吓,促进其在药物开发和精细化学制造中的使用.它的结构性特征也使它成为生物活性分子(包括蛋白抑制剂和其他治疗剂)的潜在前体.高纯度和定义明确的立体化学确保研究和工业过程中的再生.

结构式图片

相似化合物

21461-84-7 4344-84-7 32780-06-6

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ECHA物质C&L通报

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合成工艺路线路线简述

  • 合成目标产物 (R)-(-)-5-Oxotetrahydrofuran-2-Carboxylic Acid 主要起始原料 2-Ketoglutaric Acid
  • (文献来源)合成步骤主要原料 2-Ketoglutaric Acid
D-谷氨酸置于盐酸,Sodium Nitrite体系中,用 水 作为反应溶剂,化学反应生成 (R)-(-)-5-氧代-2-四氢呋喃羧酸
参考文献:富含对映体的n-(2-氯烷基)-3-乙酰氧基哌啶类化合物可能作为胆碱毒性药物.螺环叠氮鎓形成的合成和初步证据
标题:富含对映体的n-(2-氯烷基)-3-乙酰氧基哌啶类化合物可能作为胆碱毒性药物.螺环叠氮鎓形成的合成和初步证据
摘要:报道了代表乙酰胆碱的环状形式的六个对映体富集的类似物的合成.(S)-和(R)-N-(2-氯乙基)-3-乙酰氧基哌啶和(r,R)-,(r,S)-,(s,R)-和(s,S)-N从(R)-或(S)-3-羟基哌啶经五步合成了-(2-氯丙基)-3-乙酰氧基哌啶.(R)-和(S)-3-羟基哌啶可通过平行的立体定向途径从d-和1-谷氨酸进入,并通过非对映异构的tartranilic酸盐的分级重结晶而获得.((S)-N-(2-氯乙基)-3-乙酰氧基哌啶与高氯酸银反应形成乙酰胆碱的螺环叠氮基类似物,这是由叠氮基亚甲基的特征性1 H NMR位移所证明的.
DOI:10.1016/0040-4020(95)00285-G

海关参考信息

专利信息


专利号:US-6632942-B2
优先权日:2000-05-04
标题:Asymmetric synthesis of piperazic acid and derivatives thereof
发明人:ROBIDOUX ANDREA L C; SERAFINI SIRO; DIETERICH PETRA; LEONARDI STEFANIA; STIBBARD JOHN
权利人:VERTEX PHARMA
摘要:This invention provides a concise, asymmetric synthesis of piperazic acid and derivatives thereof, whereby either the (3S)- or (3R)-enantiomeric form may be obtained with high optical purity. (3S)-piperazic acid is derived from D-glutamic acid through an (R)-2,5-dihydroxyvalerate ester intermediate. After the hydroxy groups are converted to suitable leaving groups, such as mesylates, the ester is treated with a bis-protected hydrazine to provide the desired (3S)-piperazic acid derivative. The (3R) enantiomer of piperazic acid may be similarly obtained starting with L-glutamic acid. The method may also be used to obtain piperazic acid derivatives that have moderate optical purity or are racemic. By this method, piperazic acid derivatives may be obtained that are useful as intermediates for pharmacologically active compounds. For example, certain intermediates of this invention are useful for preparing caspase inhibitors, particularly inhibitors of ICE, through additional steps known in the art.

专利号:US-10035796-B2
优先权日:2014-08-14
标题:Crystalline forms of a BACE inhibitor, compositions, and their use
发明人:KAZAKEVICH IRINA; TRZASKA SCOTT; FENG TAO
权利人:MERCK SHARP & DOHME
摘要:The present invention provides a novel synthesis of verubecestat, and two novel crystalline forms of verubecestat, as well as pharmaceutically acceptable compositions thereof, each of which may be useful in treating, preventing, ameliorating, and/or delaying the onset of an Aβ pathology and/or a symptom or symptoms thereof. Non-limiting examples of such Aβ pathologies, including Alzheimer's disease, are disclosed herein.

专利号:US-10030003-B2
优先权日:2014-09-10
标 题:Synthesis of isoflavanes and intermediates thereof
发明人:BELIAEV NIKOLAI; SHAFRAN YURI
权利人:SYSTEM BIOLOGIE AG
摘要:Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.

专利号:US-5756706-A
优先权日:1991-05-21
标题 :Processes for the diastereoselective synthesis of nucleoside analogues
发明人:MANSOUR TAREK; TSE ALLAN H L
权利人:IAF BIOCHEM INT
摘要:The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity, and intermediates useful in those processes.

专利号:US-11999741-B2
优先权日:2017-05-26
标 题:Process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one
发明人:SVENSTRUP NIELS; ZHANG JUN; SUN JIKUI; CHEN YUYIN; KONG JIANSHE; MA RUJIAN; ZHANG JUNHUA; QIN LIANG; XIAO HUANMING; SUN JINXU; MENG XIAO; SUN FENGLAI; ZHU JINGYANG
权利人:CARDURION PHARMACEUTICALS INC
摘要:The present disclosure relates to processes for preparing 64(3s,4s)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7h-imidazo[1,5-a]pyrazin-8-one.

专利号:US-2003176691-A1
优先权日:2000-05-04
标 题:Asymmetric synthesis of piperazic acid and derivatives thereof
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合成参考文献


参考文献:10.1007/s002030100283
摘要:Mochizuki K. Purification and characterization of a lactonase from Burkholderia sp. R-711, that hydrolyzes (R)-5-oxo-2-tetrahydrofurancarboxylic acid. Arch Microbiol. 2001 Jun;175(6):430–4. doi: 10.1007/s002030100283.
参考文献:10.1007/bf01402924
摘要:Doolittle RE, Tumlinson JH, Proveaux AT, Heath RR. Synthesis of the sex pheromone of the Japanese beetle. Journal of Chemical Ecology. 1980 Mar;6(2):473–85. doi: 10.1007/bf01402924.
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