阳离子金（I）催化的糖基化反应，使用糖基-1,1-二甲基炔丙基碳酸酯供体。
Cationic gold(I)-catalyzed glycosylation with glycosyl -1,1-dimethylpropargyl carbamate donors.
机构信息
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, USA.
出版信息
Org Biomol Chem. 2022 Sep 14;20(35):7006-7010. doi: 10.1039/d2ob01436j.
Abstract
A mild and efficient cationic gold(I)-catalyzed -glycosylation methodology involving the use of bench-stable glycosyl -1,1-dimethylpropargyl carbamate donors has been developed. In the presence of 1-2 mol% [tris(2,4-di--butylphenyl)phosphite]gold(I) chloride and 5 mol% silver triflate, both "armed" and "disarmed" glycosyl -1,1-dimethylpropargyl carbamate donors react with various sugar acceptors at room temperature to afford the corresponding glycosides in good to excellent yields. These glycosyl -1,1-dimethylpropargyl carbamates are found to be orthogonal to regular phenyl thioglycoside donors. The utilization of this method has been demonstrated in the synthesis of a trisaccharide.
摘要
开发了一种温和高效的阳离子金（I）催化 -糖苷化方法，涉及使用稳定的糖基 -1,1-二甲基炔丙基氨基甲酸酯供体。在 1-2 mol% [三（2,4-二叔丁基苯基）膦]金（I）氯化物和 5 mol% 三氟甲磺酸银存在下，“武装”和“解除武装”的糖基 -1,1-二甲基炔丙基氨基甲酸酯供体在室温下与各种糖受体反应，以良好至优异的收率得到相应的糖苷。这些糖基 -1,1-二甲基炔丙基氨基甲酸酯与常规的苯基硫代糖苷供体正交。该方法已在三糖的合成中得到应用。
相似文献
1
Cationic gold(I)-catalyzed glycosylation with glycosyl -1,1-dimethylpropargyl carbamate donors.阳离子金（I）催化的糖基化反应，使用糖基-1,1-二甲基炔丙基碳酸酯供体。
Org Biomol Chem. 2022 Sep 14;20(35):7006-7010. doi: 10.1039/d2ob01436j.
2
Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.采用阳离子金（I）催化的涉及糖基-1,1-二甲基炔丙基碳酸酯供体的糖苷化反应合成抗原性四糖重复单元。
J Org Chem. 2024 Sep 6;89(17):12547-12558. doi: 10.1021/acs.joc.4c01484. Epub 2024 Aug 13.
3
AuCl-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature.在室温下，使用端基差向异构亚砜作为糖基供体，AuCl-AgOTf促进了O-糖基化反应。
Carbohydr Res. 2017 Jan 2;437:43-49. doi: 10.1016/j.carres.2016.11.012. Epub 2016 Nov 23.
4
Highly Reactive Glycosylation with 1-(Methylthio)thiocarbonyl Glycosyl Donors under Acidic to Neutral Reaction Conditions.在酸性至中性反应条件下，1-(甲硫基)硫代羰基糖基供体的高反应性糖基化反应
J Org Chem. 2024 Oct 4;89(19):14315-14327. doi: 10.1021/acs.joc.4c01740. Epub 2024 Sep 13.
5
o-(p-Methoxyphenylethynyl)phenyl Glycosides: Versatile New Glycosylation Donors for the Highly Efficient Construction of Glycosidic Linkages.对-(p-甲氧基苯乙炔基)苯基糖苷：用于高效构建糖苷键的新型糖苷化供体。
J Am Chem Soc. 2017 Sep 13;139(36):12736-12744. doi: 10.1021/jacs.7b07020. Epub 2017 Sep 1.
6
Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors.三价铁催化的稳定双功能去氧苯丙炔酸苷糖基供体的立体选择性合成脱氧糖苷。
Carbohydr Res. 2024 Feb;536:109051. doi: 10.1016/j.carres.2024.109051. Epub 2024 Feb 2.
7
Activation of glycosyl methylpropiolates by TfOH.三氟甲磺酸（TfOH）对甲基炔丙酸酯的活化作用。
Carbohydr Res. 2024 May;539:109106. doi: 10.1016/j.carres.2024.109106. Epub 2024 Apr 9.
8
2'-Carboxybenzyl glycosides: glycosyl donors for C-glycosylation and conversion into other glycosyl donors.2'-羧基苄基糖苷：用于C-糖基化及转化为其他糖基供体的糖基供体
Carbohydr Res. 2006 Jul 24;341(10):1708-16. doi: 10.1016/j.carres.2006.03.014. Epub 2006 Apr 17.
9
Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d- manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides.C5-羧酸酯取代基对 3-脱氧-d-甘露辛-2-酮糖酸（Kdo）硫代糖苷供体糖基化立体化学的立体定向效应：α-和β-Kdo 糖苷的立体选择性合成。
J Am Chem Soc. 2018 Mar 14;140(10):3574-3582. doi: 10.1021/jacs.7b09461. Epub 2018 Mar 6.
10
Synthesis of N-Glycosides by Silver-Assisted Gold Catalysis.银辅助金催化合成N-糖苷
Angew Chem Int Ed Engl. 2023 Feb 1;62(6):e202214167. doi: 10.1002/anie.202214167. Epub 2022 Dec 28.
引用本文的文献
1
ZnI-Mediated -Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in -Selective Glycosylations.碘化锌介导的各种受限糖基供体的α-糖基化反应：α-选择性糖基化反应的最新进展
Molecules. 2024 Oct 4;29(19):4710. doi: 10.3390/molecules29194710.
2
Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.采用阳离子金（I）催化的涉及糖基-1,1-二甲基炔丙基碳酸酯供体的糖苷化反应合成抗原性四糖重复单元。
J Org Chem. 2024 Sep 6;89(17):12547-12558. doi: 10.1021/acs.joc.4c01484. Epub 2024 Aug 13.
3
Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoate donors.通过使用糖基邻-2,2-二甲氧基羰基环丙基苯甲酸盐供体的催化应变释放糖基化反应，高效且多功能地形成糖苷键。
Nat Commun. 2023 Jul 7;14(1):4010. doi: 10.1038/s41467-023-39619-7.
本文引用的文献
1
A "Traceless" Directing Group Enables Catalytic S2 Glycosylation toward 1,2--Glycopyranosides.一种“无痕”导向基团实现了 1,2-糖苷的催化 S2 糖基化。
J Am Chem Soc. 2021 Aug 11;143(31):11908-11913. doi: 10.1021/jacs.1c04584. Epub 2021 Jul 28.
2
Binuclear Tridentate Hemilabile Copper(I) Catalysts for Utilization of CO into Oxazolidinones from Propargylic Amines.用于将一氧化碳从炔丙基胺转化为恶唑烷酮的双核三齿半不稳定铜（I）催化剂
J Org Chem. 2020 Dec 4;85(23):15197-15212. doi: 10.1021/acs.joc.0c02065. Epub 2020 Nov 9.
3
Transition metal catalyzed glycosylation reactions - an overview.过渡金属催化的糖基化反应——概述。
Org Biomol Chem. 2020 Nov 25;18(45):9160-9180. doi: 10.1039/d0ob01782e.
4
Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors.金（I）催化的糖基烯酸酯作为供体的糖苷化反应。
Org Lett. 2019 Dec 6;21(23):9693-9698. doi: 10.1021/acs.orglett.9b03851. Epub 2019 Nov 20.
5
Gold(I)-Catalyzed Glycosylation with Glycosyl o-Alkynylbenzoates as Donors.金（I）催化糖基化反应：以糖基-o-炔基苯甲酸酯作为供体。
Acc Chem Res. 2018 Feb 20;51(2):507-516. doi: 10.1021/acs.accounts.7b00573. Epub 2018 Jan 3.
6
Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the cellular envelope by glycosyl carbonate donors.通过碳酸糖基供体快速合成细胞膜的二十一糖基甘露糖封端阿拉伯甘露聚糖。
Chem Sci. 2017 Mar 1;8(3):2033-2038. doi: 10.1039/c6sc04866h. Epub 2016 Nov 15.
7
Stable Alkynyl Glycosyl Carbonates: Catalytic Anomeric Activation and Synthesis of a Tridecasaccharide Reminiscent of Mycobacterium tuberculosis Cell Wall Lipoarabinomannan.稳定的炔基糖基碳酸酯：催化的端基异构激活和十三糖的合成，类似于结核分枝杆菌细胞壁脂阿拉伯甘露聚糖。
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7786-91. doi: 10.1002/anie.201511695. Epub 2016 Feb 16.
8
Recent Advances in Transition Metal-Catalyzed Glycosylation.过渡金属催化糖基化的最新进展
ACS Catal. 2012 Aug 3;2(8):1563-1595. doi: 10.1021/cs3002513. Epub 2012 Jun 14.
9
Characterization of the isochromen-4-yl-gold(I) intermediate in the gold(I)-catalyzed glycosidation of glycosyl ortho-alkynylbenzoates and enhancement of the catalytic efficiency thereof.异色满-4-基-金（I）中间体在金（I）催化的邻炔基苯甲酸糖基酯糖苷化反应中的表征及其催化效率的提高
Angew Chem Int Ed Engl. 2011 Aug 29;50(36):8329-32. doi: 10.1002/anie.201103409. Epub 2011 Jul 20.
10
Gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors: general scope and application in the synthesis of a cyclic triterpene saponin.金（I）催化的糖基化反应，使用糖基邻炔基苯甲酸酯作为供体：广泛的反应范围和在环三萜皂苷合成中的应用。
Chemistry. 2010 Feb 8;16(6):1871-82. doi: 10.1002/chem.200902548.
Zotero 插件