CAS: 15667-21-7; (3R,4R)-3,4-Dihydroxydihydrofuran-2(3H)-One

该化合物是一个有机循环碳酸盐衍生物,其特征是3和4个位置的立体特定氢氧化物组.该化合物是有机合成的多功能中间体,特别是在准备抗生素纯化药品和精细化学物时.其僵硬的氧化氯酮框架和二醇功能使得选择性衍生化,使其对不对称合成和催化剂设计具有价值.该化合物在温和条件下的高度立体化学纯度和稳定性增强了其在复杂的分子构造中的效用. 此外,它与绿色化学原理的兼容性,例如生物降解潜力,进一步强调了其在可持续合成应用中的关联性.

结构式图片

相似化合物

19444-84-9 52079-23-9 5336-08-3

上下游产品

CAS号134-03-2 维生素C钠 | CAS号89-65-6 D-异抗坏血酸 | CAS号7152-74-1 [(3R,4S)-4-hydr... | CAS号25581-41-3 2,3-O-异亚丙基-D-赤酮酸内酯 | CAS号50-81-7 抗坏血酸 | CAS号219788-23-5 1,2:3,4-Di-O-is... | CAS号488-16-4 D-赤藓酸钾盐 | CAS号10323-20-3 D-阿拉伯糖 | CAS号497-23-4 2(5H)-呋喃酮 | CAS号25581-41-3 2,3-O-异亚丙基-D-赤酮酸内酯 | CAS号107-93-7 巴豆酸 | CAS号7425-21-0 3-iodobutanoic acid

合成工艺路线路线简述

    Ascorbinsaeure置于双氧水,Sodium Carbonate体系中,用77%的收率获得(3R,4R)-(-)-D-赤酮酸内酯
    参考文献:D-Erythronolactone As A C4 Building Unit. Part 2.1 A Short And Efficient Synthesis Of Both Enantiomers Of Epi-Muricatacin,A Diastereoisomer Of The Native Acetogenin From Annona Muricata
    标题:D-Erythronolactone As A C4 Building Unit. Part 2.1 A Short And Efficient Synthesis Of Both Enantiomers Of Epi-Muricatacin,A Diastereoisomer Of The Native Acetogenin From Annona Muricata
    摘要:两种对映体epimuricatacin的正(+)和负(-)2已由2,3-O-异丙腈-D-赤藓糖7制备而成.这些对映体(+)和(-)2以非常好的收率和高的非对映体及对映纯度获得.合成的目标是从一个手性前体获得目标分子的两种对映体.这得以实现是因为引入两种不同侧链的反应序列是可互换的.
    Doi:10.1039/a607158I

    海关参考信息

    专利信息


    专利号:US-2004018598-A1
    优先权日:2000-05-30
    标题 :Bio-intermediates for use in the chemical synthesis of polyketides
    发明人:SANTI DANIEL; ASHLEY GARY; MYLES DAVID C
    摘要:The present invention relates to compounds made by a subset of modules from one or more polyketide synthase (“PKSâ€?) genes that are used as starting material in the chemical synthesis of novel molecules, particularly naturally occurring polyketides or derivatives thereof. The biologically derived intermediates (“bio-intermediatesâ€?) generally represent particularly difficult compounds to synthesize using traditional chemical approaches due to one or more stereocenters. In one aspect of the invention, an intermediate in the synthesis of epothilone is provided that feeds into the synthetic protocol of Danishefsky and co-workers. In another aspect of the invention, intermediates in the synthesis of discodermolide are provided that feed into the synthetic protocol of Smith and co-workers. By taking advantage of the inherent stereochemical specificity of biological processes, the syntheses of key intermediates and thus the overall syntheses of compounds like epothilone and discodermolide are greaty simplified.

    专利号:US-9862745-B2
    优先权日:2004-03-30
    标题 :Synthesis of boronic ester and acid compounds
    发明人:AMMOSCATO VINCE; BISHOP JOHN E; CHIU FANG-TING; GEISER ACHIM; GOMEZ JEAN-MARC; HETT ROBERT; KOELLNER CHRISTOPH; KULKARNI VITHALANAND R; LO YOUNG; MUNK STEPHEN; PICKERSGILL I FRASER
    权利人:MILLENNIUM PHARM INC; MILLENNIUM PHARM INC
    摘要:The invention relates to the synthesis of boronic ester and acid compounds. More particularly, the invention provides improved synthetic processes for the large-scale production of boronic ester and acid compounds, including the peptide boronic acid proteasome inhibitor bortezomib.

    专利号:US-2009197311-A1
    优先权日:2006-06-20
    标题:Method for the production of simvastatin
    发明人:BERG MARCO ALEXANDER VAN DEN; HANS MARCUS; STREEKSTRA HUGO
    权利人:BERG MARCO ALEXANDER VAN DEN; HANS MARCUS; STREEKSTRA HUGO
    摘要:The present invention provides a fermentative process for the synthesis of simvastatin by providing a host capable of incorporating the 2,2-dimethylbutyrate side chain into simvastatin, i.e. by customizing a polyketide synthase gene optimized for synthesis and/or incorporation of 2,2-dimethylbutyrate; optionally feeding said host with the appropriate substrate for 2,2-dimethylbutyrate synthesis; fermenting said host to obtain simvastatin or analogues or derivatives thereof, i.e. by producing simvastatin on an industrial scale by a fed-batch process.

    专利号:US-2008044860-A1
    优先权日:2003-11-28
    标题 :Polyketides and Their Synthesis
    发明人:GAISSER SABINE; HAYDOCK STEPHEN FREDERICK; LEADLAY PETER FRANCIS; MCARTHUR HAMISH ALASTAIR IRVIN
    权利人:GAISSER SABINE; HAYDOCK STEPHEN FREDERICK; LEADLAY PETER FRANCIS; MCARTHUR HAMISH ALASTAIR IRVIN
    摘要:Macrolides particularly erythromycins and azithromycins, having O-mycaminosyl or O-angolosaminyl groups, particularly at the 5 -position, are produced using a gene cassette comprising a combination of genes which, in an appropriate strain background, are able to direct the synthesis of mycaminose or angolosamine and to direct its subsequent transfer to an aglycone or pseudoaglycone. Synthetic genes may comprise one or more of angMIII, angMI, angB, angAI, angAII, angorf14, angorf4, tylMIII, tylMI, tylB, tylAI, tylAII, eryCVI, spnO, eryBVI, eryK, tyl Ia and ery G. Glycosyltransfer genes may comprise one or more of eryCIII, tylMII, angMII, desVII, eryBV, spnP and midI.

    专利号:US-5187279-A
    优先权日:1990-07-27
    标题:Synthesis of (-) swainsonine and intermediate compounds employed in such synthesis
    发明人:CHA JIN K; BENNETT III RICHARD B
    权利人:CHA JIN K; BENNETT III RICHARD B
    摘要:(-)-Swainsonine is prepared by the steps of first reacting a compound having the formula: ##STR1## wherein each R 2 is lower alkyl, with (4-carbalkoxybutyl) triphenylphosphonium bromide in a strong base to obtain an alcohol having the formula: ##STR2## wherein R 2 is as defined above and R is C 1 -C 8 alkyl; the alcohol is then reacted with methanesulfonyl chloride or p-toluenesulfonyl chloride or benzenesulfonyl chloride in the presence of a tertiary amine to obtain the corresponding sulfonate. Heating the sulfonate with an azide in an organic solvent yields an imine having the formula: ##STR3## wherein R 2 and R are ad defined above. Treating the imine with an inorganic base, in aqueous alcohol provides upon acidification, the corresponding acid. Heating the acid at reflux temperature in organic solvent, yields an enamide having the formula: ##STR4## wherein R 2 is as defined above. Treating the enamide with diborane followed by reaction with hydrogen peroxide provides a protected swainsonine having the formula: ##STR5## which upon acid hydrolysis gives swainsonine.

    专利号:WO-9006311-A1
    优先权日:1988-11-29
    标 题 :Synthesis of (-)-swainsonine and intermediate compounds employed in such synthesis
    发明人:CHA JIN KUN; BENNETT RICHARD BERNARD III
    权利人:UNIV VANDERBILT
    摘要:A method of synthesizing swainsonine and its analogues employing a unique intermediate imine and a unique intermediate enamide.
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    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: Wen Shan Yew, Et Al. Evolution Of Enzymatic Activities In The Enolase Superfamily: L-Fuconate Dehydratase From Xanthomonas Campestris. Biochemistry. 2006 Dec 12;45(49):14582-97.

    合成参考文献


    摘要:Zhanel GG, Hisanaga T, Wierzbowski A, Hoban DJ. Telithromycin in the treatment of acute bacterial sinusitis, acute exacerbations of chronic bronchitis, and community-acquired pneumonia. Ther Clin Risk Manag. 2006 Mar;2(1):59–75.
    参考文献:10.1021/ja048836f
    摘要:Lee HY, Chung HS, Hang C, Khosla C, Walsh CT, Kahne D, Walker S. Reconstitution and characterization of a new desosaminyl transferase, EryCIII, from the erythromycin biosynthetic pathway. J Am Chem Soc. 2004 Aug 18;126(32):9924–5. doi: 10.1021/ja048836f.
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