CAS: 102191-92-4; (Tert-Butyldimethylsilyloxy)Acetaldehyde

该化合物是一种有机硅化合物,其特点是,存在一种与乙型甲型乙型乙酰二甲基硅氧基化合物相连的基质组,该化合物一般看起来无色,是黄色的无色液体,在标准条件下以其稳定性著称.该化合物具有硅状醚功能组,具有独特的反应性和溶解性,在有机合成中非常有用,特别是在保护酒精和甲型甲状腺类时尤其如此.乙型丁基甲基硅酸基化合物组增强了该化合物对水解的抗药性,允许合成途径有选择地反应.此外,甲型戊型乙胺功能组的存在有助于其再活动,使其能够参与各种化学变异,例如核糖类添加物.这一化合物经常用于合成更为复杂的有机分子,并可以与实验室标准安全防范措施一起加以处理.与许多有机硅混合物一样,重要的是考虑其与其他化学反应中的试剂和溶剂的兼容性.

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合成工艺路线路线简述

    (Z)-4-(Tert-Butyldimethylsilyloxy)But-2-En-1-Ol置于臭氧,三苯基膦体系中,用 二氯甲烷 用作溶剂,化学反应生成叔丁基二甲基硅氧烷基乙醛
    参考文献:来自短甲藻的新型海洋环醚生物碱 Brevisamide 的全合成和结构确认
    标题:来自短甲藻的新型海洋环醚生物碱 Brevisamide 的全合成和结构确认
    摘要:从顺式-丁-2-烯-1,4-二醇开始,在21个线性步骤中完成了短酰胺( 1 )的第一次全合成.合成亮点是醚环片段和二烯醇侧链之间的 Suzuki-Miyaura 偶联.该结果证实了从短鞭毛藻karenia Brevis中分离的1的结构.
    Doi:10.1021/ol802426V

    专利信息


    专利号:WO-2009030733-A1
    优先权日:2007-09-04
    标 题 :Method for the synthesis of 4-alkoxy-, 4-hydroxy- and 4-aryloxy-substituted tetrahydro-furo[3,4-b]furan-2(3h)-one compounds
    发明人:QUAEDFLIEG PETER JAN LEONARD MARIO; ALSTERS PAULUS LAMBERTUS; STRAATMAN HENRICUS MARTINUS MARIO; HANBAUER MARTIN HELMUT FRIEDRICK
    权利人:DSM IP ASSETS BV; QUAEDFLIEG PETER JAN LEONARD MARIO; ALSTERS PAULUS LAMBERTUS; STRAATMAN HENRICUS MARTINUS MARIA GERARDUS; HANBAUER MARTIN HELMUT FRIEDRI
    摘要:The present invention relates to a method for the synthesis of enantiomerically and diastereomerically enriched 4-alkoxy-, 4-hydroxy- or 4-aryloxy- substituted tetrahydro-furo[3,4-b]furan-2(3H)-ones by aldol coupling of a suitable hydroxyl-protected hydroxy-acetaldehyde and 4-oxobutanoic acid or an ester thereof, and subsequent removal of the protecting group from the aldol compound and (optionally simultaneous) cyclizations and acetal formation under acidic conditions in the presence of an alcohol, followed by optional isolation of the desired compounds. The invention also relates to compounds according to formulae [Xl] and [XII].

    专利号:US-4309346-A
    优先权日:1980-03-27
    标 题:Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
    发明人:CHRISTENSEN BURTON G; RATCLIFFE RONALD W; SALZMANN THOMAS N
    权利人:MERCK & CO INC
    摘要:Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via intermediates II and III: I II III wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6 and R7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' is hydrogen or a protecting group; and Ra, Rb and Rc are independently selected from alkyl, aryl and aralkyl.

    专利号:US-4383946-A
    优先权日:1980-03-27
    标题:Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals
    发明人:CHRISTENSEN BURTON G; RATCLIFFE RONALD W; SALZMANN THOMAS N
    权利人:MERCK & CO INC
    摘要:Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via central intermediates II and III: I II III wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6, R7 and R8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1'and Re are hydrogen, or a readily removable protecting group; Ra, Rb and Rc are selected from alkyl, aryl or aralkyl.

    专利号:WO-2010024762-A1
    优先权日:2008-08-26
    标题 :PREPARATION OF β-PHENYL-ISOSERINE DERIVATIVES
    发明人:CORDOVA ARMANDO; DZIEDZIC PAWEL; VESELY JAN
    权利人:ORGANOCLICK AKTIEBOLAG; CORDOVA ARMANDO; DZIEDZIC PAWEL; VESELY JAN
    摘要:A process for stereoselective synthesis of a β-phenylisoserine comprises reacting a carbonyl imine R-C=N-CO-OR 1 with a protected α- oxyaldehyde X 1 O-CH 2 CHO in the presence of a chiral amine catalyst and oxidizing aldehyde so obtained.

    专利号:US-2018111956-A1
    优先权日:2015-03-25
    标题:Synthesis of desosamines

    专利号:US-7999090-B2
    优先权日:2000-07-07
    标 题:Fungal cell wall synthesis gene
    发明人:TSUKAHARA KAPPEI; HATA KATSURA; SAGANE KOJI; NAKAMOTO KAZUTAKA; TSUCHIYA MAMIKO; WATANABE NAOAKI; OHBA FUMINORI; TSUKADA ITARU; UEDA NORIHIRO; TANAKA KEIGO; KAI JUNKO
    权利人:EISAI R&D MAN CO LTD
    摘要:The present invention provides isolated DNA encoding a GWT1 protein having activity to confer resistance of a fungus against a compound of formula Ia, and wherein a defect of a function of the GWT1 protein leads to a decrease in the amount of a glycosylphosphatidylinositol (GPI)-anchored protein in the cell wall of a fungus.
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    主要参考文献

    [参考文献]: Ignace Louis, Et Al. Enantioselective Total Synthesis Of (-)-Dactylolide. Org Lett. 2006 Mar 16;8(6):1117-20.
    [参考文献]: Ritsuo Imashiro, Et Al. One-Pot Enantioselective Syntheses Of Iminosugar Derivatives Using Organocatalytic Anti-Michael-Anti-Aza-Henry Reactions. Org Lett. 2010 Nov 19;12(22):5250-3.

    合成参考文献


    摘要:Okamoto, K.; Ohe, K., Science of Synthesis Knowledge Updates, (2020) 1, 67.
    摘要:Li, Y.; Xie, W.; Jiang, X., Science of Synthesis Knowledge Updates, (2016) 2, 82.
    摘要:Schneider, C.; Sickert, M., Science of Synthesis Knowledge Updates, (2017) 3, 341.
    摘要:Zhang, Z.; Tong, R., Science of Synthesis Knowledge Updates, (2019) 2, 374.
    摘要:Schleicher, K. D.; Jamison, T. F., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 550.
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