一种稳定的、可商购的亚磺酰氯，用于与三氟甲磺酸银联合活化硫代糖苷。
A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate.
作者信息
Crich David, Cai Feng, Yang Fan
机构信息
Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.
出版信息
Carbohydr Res. 2008 Jul 21;343(10-11):1858-62. doi: 10.1016/j.carres.2008.03.002. Epub 2008 Mar 10.
Abstract
p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 degrees C in CH(2)Cl(2).
摘要
对硝基苯亚磺酰氯是一种稳定的市售亚磺酰氯，它与三氟甲磺酸银一起，能在-78℃的二氯甲烷中顺利地活化多种硫代糖苷用于糖基化反应。
相似文献
1
A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate.
Carbohydr Res. 2008 Jul 21;343(10-11):1858-62. doi: 10.1016/j.carres.2008.03.002. Epub 2008 Mar 10.
2
O,O-dimethylthiophosphonosulfenyl bromide-silver triflate: a new powerful promoter system for the preactivation of thioglycosides.
Org Biomol Chem. 2011 Jan 21;9(2):616-22. doi: 10.1039/c0ob00380h. Epub 2010 Nov 10.
3
S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides.
Org Lett. 2000 Dec 14;2(25):4067-9. doi: 10.1021/ol006715o.
4
2-Nitro-thioglycosides: α- and β-selective generation and their potential as β-selective glycosyl donors.
Org Lett. 2015 Mar 20;17(6):1421-4. doi: 10.1021/acs.orglett.5b00295. Epub 2015 Mar 5.
5
Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf.
Carbohydr Res. 2012 Jun 1;354:40-8. doi: 10.1016/j.carres.2012.03.024. Epub 2012 Apr 7.
6
In(III) triflate-mediated solvent-free synthesis and activation of thioglycosides by ball milling and structural analysis of long chain alkyl thioglycosides by TEM and quantum chemical methods.
J Org Chem. 2014 Apr 18;79(8):3427-39. doi: 10.1021/jo5001753. Epub 2014 Apr 8.
7
DIDMH in combination with triflic acid - A new promoter system for thioglycoside glycosyl donors.
Carbohydr Res. 2018 Jan 2;455:86-91. doi: 10.1016/j.carres.2017.11.012. Epub 2017 Nov 21.
8
A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor.
Chem Commun (Camb). 2015 Aug 18;51(64):12803-6. doi: 10.1039/c5cc03617h.
9
1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.
J Am Chem Soc. 2001 Sep 19;123(37):9015-20. doi: 10.1021/ja0111481.
10
Odorless benzenethiols in synthesis of thioglycosides and its application for glycosylation reactions.
Bioorg Med Chem Lett. 2006 Nov 15;16(22):5736-9. doi: 10.1016/j.bmcl.2006.08.095. Epub 2006 Sep 12.
引用本文的文献
1
Exploration of the Oxazolidinthione Protecting System for the Synthesis of Sialic Acid Glycosides.
J Carbohydr Chem. 2013;32(5-6):324-335. doi: 10.1080/07328303.2013.804081. Epub 2013 Sep 2.
2
Capture of uropathogenic E. coli by using synthetic glycan ligands specific for the pap-pilus.
Chembiochem. 2013 Jan 21;14(2):251-9. doi: 10.1002/cbic.201200582. Epub 2013 Jan 10.
3
Chemical synthesis and immunological evaluation of the inner core oligosaccharide of Francisella tularensis.
J Am Chem Soc. 2012 Aug 29;134(34):14255-62. doi: 10.1021/ja306274v. Epub 2012 Aug 16.
4
Chemical synthesis of glycosylphosphatidylinositol anchors.
Adv Carbohydr Chem Biochem. 2012;67:137-219. doi: 10.1016/B978-0-12-396527-1.00004-8.
5
Total synthesis of (+)-sieboldine a: evolution of a pinacol-terminated cyclization strategy.
J Org Chem. 2013 Jan 4;78(1):9-34. doi: 10.1021/jo300872y. Epub 2012 Jun 26.
6
Chemical synthesis and functionalization of clickable glycosylphosphatidylinositol anchors.
Chem Sci. 2011;2(12):2342-2352. doi: 10.1039/C1SC00440A.
7
Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.
J Org Chem. 2011 Nov 18;76(22):9193-209. doi: 10.1021/jo2017026. Epub 2011 Oct 4.
8
Versatile set of orthogonal protecting groups for the preparation of highly branched oligosaccharides.
Org Lett. 2010 Oct 15;12(20):4636-9. doi: 10.1021/ol101951u.
9
Synthesis of a novel alpha-galactosyl ceramide haptenated-lipid antigen, a useful tool in demonstrating the involvement of iNKT cells in the production of antilipid antibodies.
Bioconjug Chem. 2010 Apr 21;21(4):741-7. doi: 10.1021/bc9005255.
10
Stereocontrolled synthesis of D- and L-beta-rhamnopyranosides with 4-O-6-S-alpha-cyanobenzylidene-protected 6-thiorhamnopyranosyl thioglycosides.
J Org Chem. 2009 Jan 16;74(2):773-81. doi: 10.1021/jo8022439.
本文引用的文献
1
A new, powerful glycosylation method: activation of thioglycosides with dimethyl disulfide-triflic anhydride.
Org Lett. 2007 Oct 25;9(22):4647-50. doi: 10.1021/ol702139u. Epub 2007 Oct 2.
2
Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates.
Org Lett. 2007 Apr 12;9(8):1613-5. doi: 10.1021/ol070449y. Epub 2007 Mar 9.
3
O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.
J Org Chem. 2007 Mar 30;72(7):2387-91. doi: 10.1021/jo062431r. Epub 2007 Mar 6.
4
Chemoselective synthesis of oligosaccharides of 2-deoxy-2-aminosugars.
J Org Chem. 2007 Feb 16;72(4):1480-3. doi: 10.1021/jo062171d. Epub 2007 Jan 25.
5
Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane.
Org Lett. 2006 Mar 2;8(5):959-62. doi: 10.1021/ol060030s.
6
Environmentally benign beta-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10.
Carbohydr Res. 2005 Feb 28;340(3):337-53. doi: 10.1016/j.carres.2004.11.025.
7
Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses.
Carbohydr Res. 2004 Dec 27;339(18):2821-33. doi: 10.1016/j.carres.2004.10.002.
8
Iterative one-pot synthesis of oligosaccharides.
Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5221-4. doi: 10.1002/anie.200460176.
9
Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.
Org Lett. 2003 May 1;5(9):1519-22. doi: 10.1021/ol034312t.
10
Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno Series.
J Org Chem. 1999 Jun 25;64(13):4926-4930. doi: 10.1021/jo990243d.
Zotero 插件