Palladium(II)-assisted activation of thioglycosides.
Journal
Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995
Informations de publication
Date de publication:
11 03 2021
11 03 2021
Historique:
pubmed:
19
2
2021
medline:
20
7
2021
entrez:
18
2
2021
Statut:
ppublish
Résumé
Described herein is the first example of glycosidation of thioglycosides in the presence of palladium(ii) bromide. While the activation with PdBr2 alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylations were performed in the presence of propargyl bromide as an additive. Preliminary mechanistic studies suggest that propargyl bromide assists the reaction by creating an ionizing complex, which accelerates the leaving group departure. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this new reaction. Selective and chemoselective activation of thioglycosides over other leaving groups has also been explored.
Identifiants
pubmed: 33599667
doi: 10.1039/d1ob00004g
pmc: PMC8142060
mid: NIHMS1699744
doi:
Substances chimiques
Disaccharides
0
Thioglycosides
0
Palladium
5TWQ1V240M
Pargyline
9MV14S8G3E
propargyl bromide
F3H7ZXK9ZU
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
2044-2054Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM111835
Pays : United States
Références
J Org Chem. 2010 Mar 5;75(5):1783-6
pubmed: 20136154
Carbohydr Res. 1985 Jun 15;139:105-13
pubmed: 4028047
J Am Chem Soc. 2001 Sep 12;123(36):8766-72
pubmed: 11535081
Org Lett. 2015 Sep 18;17(18):4448-51
pubmed: 26349759
Adv Carbohydr Chem Biochem. 2009;62:161-250
pubmed: 19501706
Chem Commun (Camb). 2009 Nov 14;(42):6379-81
pubmed: 19841783
Chem Rev. 2018 Sep 12;118(17):8285-8358
pubmed: 29969248
Org Lett. 2000 Dec 14;2(25):4067-9
pubmed: 11112645
J Org Chem. 1996 Nov 1;61(22):7711-7718
pubmed: 11667725
J Org Chem. 2009 Feb 20;74(4):1650-7
pubmed: 19161277
J Org Chem. 2016 Jul 15;81(14):5949-62
pubmed: 27295299
Carbohydr Res. 2011 Sep 6;346(12):1371-88
pubmed: 21663897
J Am Chem Soc. 2021 Jan 13;143(1):17-34
pubmed: 33350830
Chemistry. 2021 Jan 4;27(1):354-361
pubmed: 32804435
J Am Chem Soc. 2004 Mar 24;126(11):3428-9
pubmed: 15025462
J Org Chem. 2007 Jul 20;72(15):5870-3
pubmed: 17580902
Angew Chem Int Ed Engl. 2001 Mar 2;40(5):946-949
pubmed: 11241655
Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8441-5
pubmed: 23813696
Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5221-4
pubmed: 15455432
Org Lett. 2004 Nov 25;6(24):4515-8
pubmed: 15548064
Org Lett. 2015 Nov 20;17(22):5606-9
pubmed: 26540490
J Am Chem Soc. 2012 Feb 15;134(6):2906-9
pubmed: 22296656
Org Lett. 2001 Mar 22;3(6):913-5
pubmed: 11263914
Acc Chem Res. 2015 May 19;48(5):1450-63
pubmed: 25871824
Chem Soc Rev. 2018 Oct 29;47(21):7954-7984
pubmed: 29993057
J Am Chem Soc. 2018 Sep 26;140(38):11942-11953
pubmed: 30125122
Org Lett. 2004 Mar 4;6(5):839-41
pubmed: 14986988
Org Lett. 2013 Jan 4;15(1):30-3
pubmed: 23256636
ACS Catal. 2012 Aug 3;2(8):1563-1595
pubmed: 22924154
Org Lett. 2007 Jan 18;9(2):263-6
pubmed: 17217280
Angew Chem Int Ed Engl. 2016 May 23;55(22):6515-9
pubmed: 27086646
J Org Chem. 2008 Feb 1;73(3):794-800
pubmed: 18184010
Chem Rev. 2018 Sep 12;118(17):8105-8150
pubmed: 29953217
J Am Chem Soc. 2019 Jul 31;141(30):11775-11780
pubmed: 31314513
Org Biomol Chem. 2016 Mar 21;14(11):3159-69
pubmed: 26911322
Chem Sci. 2016 Jul 1;7(7):4259-4263
pubmed: 30090287
Chemistry. 2018 Mar 2;24(13):3271-3282
pubmed: 29314341
Beilstein J Org Chem. 2012;8:597-605
pubmed: 22563357
Angew Chem Int Ed Engl. 2017 Mar 20;56(13):3640-3644
pubmed: 28211228
Org Lett. 2003 May 1;5(9):1519-22
pubmed: 12713313
Org Lett. 2010 Dec 17;12(24):5628-31
pubmed: 21087037
J Am Chem Soc. 2006 Aug 2;128(30):9620-1
pubmed: 16866502
J Am Chem Soc. 2001 Sep 19;123(37):9015-20
pubmed: 11552809
Angew Chem Int Ed Engl. 2009;48(11):1900-34
pubmed: 19173361
Chem Rev. 2000 Dec 13;100(12):4283-318
pubmed: 11749349
Angew Chem Int Ed Engl. 2015 Jan 7;54(2):604-7
pubmed: 25366278
Carbohydr Res. 2012 Aug 1;357:47-52
pubmed: 22739243
Dalton Trans. 2010 Jul 21;39(27):6327-38
pubmed: 20517543
J Org Chem. 2014 Oct 17;79(20):9444-50
pubmed: 25137149
Chem Commun (Camb). 2008 Nov 21;(43):5633-5
pubmed: 18997976
J Org Chem. 2014 Dec 5;79(23):11473-82
pubmed: 25406990
Angew Chem Int Ed Engl. 2018 Jun 4;57(23):6915-6920
pubmed: 29663659
J Am Chem Soc. 2003 Jul 23;125(29):8714-5
pubmed: 12862452
Carbohydr Res. 2019 Dec 1;486:107824
pubmed: 31585319
Carbohydr Res. 2015 Feb 11;403:13-22
pubmed: 25015586
Glycobiology. 2017 Jan;27(1):3-49
pubmed: 27558841