CAS: 204255-06-1; 5-Azido Oseltamivir

该化合物是一种复杂的有机化合物,其独特的结构特征包括环己环和多种功能组,如乙酰胺组和乙酰胺组,乙氧基替代组的存在有助于其疏水特性,而乙酰丙胺组的存在则具有再活动的潜力,特别是在点击化学应用方面.(3R,4R,5S)配置显示的立体化学显示的原子的具体空间安排,可影响该化合物的生物活动和与其他分子的相互作用.该化合物可能具有与医药化学有关的特性,特别是在研制药品或作为生物化学探测器方面.其合成和处理需要仔细考虑由于乙酰胺组而导致的安全议定书,在某些条件下,该组可能具有敏感性和潜在爆炸性.

结构式图片

MSDS等安全信息

    上下游产品

    CAS号1149345-89-0 ethyl (3R,4R,5R... | CAS号75-36-5 乙酰氯 | CAS号204255-04-9 N-Desacetyl 5-A... | CAS号1001085-29-5 ethyl (3R,4S,5R... | CAS号1132659-99-4 (3R,4S,5R)-4-ac... | CAS号1163128-59-3 (3R,4R,5S)-ethy... | CAS号108-24-7 乙酸酐 | CAS号196618-13-0 奥司他韦 | CAS号204255-11-8 磷酸奥司他韦

    合成工艺路线路线简述

    • 合成目标产物 Ethyl (3R,4R,5S)-4-Acetamido-5-Azido-3-(1-Ethylpropoxy)Cyclohex-1-Ene-1-Carboxylate 主要起始原料 Oseltamivir
    • (文献来源)合成步骤主要原料 Oseltamivir
    📜D-甘露糖置于吡啶,咪唑,盐酸,4-二甲氨基吡啶,Sodium Periodate,Sodium Azide,硼烷四氢呋喃络合物,草酰氯,硫酸,10% Pd/c,四丁基氟化铵,水,氢气,四氯化钛,Copper(II) Bis(Trifluoromethanesulfonate),Sodium Hydride,二甲基亚砜,三乙胺,三苯基膦体系中,用 四氢呋喃,甲醇,乙醇,二氯甲烷,水,N,N-二甲基甲酰胺 用作溶剂,化学反应 187.92H,反应生成5-叠氮奥塞米韦
    参考文献:Org/10.1016/j.Tetlet.2012.08.143
    标题:Org/10.1016/j.Tetlet.2012.08.143
    摘要:
    Doi:Org/10.1016/j.Tetlet.2012.08.143

    海关参考信息

    专利信息


    专利号:US-7888337-B2
    优先权日:2007-08-31
    标 题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
    发明人:WONG CHI-HUEY; FANG JIM-MIN; SHIE JIUN-JIE; CHENG YIH-SHYUN EDMOND; JAN JIA-TSRONG
    权利人:ACADEMIA SINICA
    摘要:Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu®, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and >20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5 -cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis-dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.

    专利号:WO-9955664-A1
    优先权日:1998-04-24
    标 题 :Preparation of carbocyclic compounds
    发明人:BECKER MARK W; CHAPMAN HARLAN H; KELLY DAPHNE E; KENT KENNETH M; LEW WILLARD; LOUIE MICHAEL S; MCGEE LAWRENCE R; PRISBE ERNEST J; POSTICH MICHAEL J; ROHLOFF JOHN C; SCHULTZE LISA M; YU RICHARD H; ZHANG LIJUN
    权利人:GILEAD SCIENCES INC; BECKER MARK W; CHAPMAN HARLAN H; KELLY DAPHNE E; KENT KENNETH M; LEW WILLARD; LOUIE MICHAEL S; MCGEE LAWRENCE R; PRISBE ERNEST J; POSTICH MICHAEL J; ROHLOFF JOHN C; SCHULTZE LISA M; YU RICHARD H; ZHANG LIJUN
    摘要:The present invention provides new synthetic methods and compositions. In particular, new methods of preparing intermediates useful in the synthesis of neuraminidase inhibitors and compositions useful as intermediates that are themselves useful in the synthesis of neuraminidase inhibitors are provided.

    专利号:US-8304553-B2
    优先权日:2007-12-19
    标题:Method of forming oseltamivir and derivatives thereof
    发明人:LIU XUEWEI; MA JIMEI
    权利人:LIU XUEWEI; MA JIMEI; UNIV NANYANG TECH
    摘要:A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R 1 -R 3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R 4 , R 11 and R 12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R 5 and R 6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R 7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).

    专利号:WO-2009029888-A2
    优先权日:2007-08-31
    标题:Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity

    专利号:US-2010113397-A1
    优先权日:2007-08-31
    标 题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity

    专利号:AU-2008292859-B2
    优先权日:2007-08-31
    标题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity

    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:Azoacetylenes For The Synthesis Of Arylazotriazole Photoswitches
    作者:Patrick Pfaff,Felix Anderl,Moritz Fink,Moritz Balkenhohl,Erick M. Carreira |发布日期:2021.9.15
    摘要:Tips-Acetylene To Aryldiazonium Tetrafluoroborate Salts Gives A Wide Range Of Azoacetylenes, Constituting An Underexplored Class Of Stable Intermediates. In Situ Desilylation Transiently Leads To Terminal Arylazoacetylenes That Undergo Copper-Catalyzed Cycloadditions (Cuaac) With A Diverse Collection Of Organoazides. These Include Complex Molecules Derived From Natural Products Or Drugs, Such As Colchicine

    合成参考文献


    摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2008).
    摘要:Bräse, S.; Lesch, B.; Zimmermann, V., Science of Synthesis, (2010) 41, 595.
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