α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
05 04 2019
05 04 2019
Historique:
pubmed:
28
2
2019
medline:
28
2
2019
entrez:
28
2
2019
Statut:
ppublish
Résumé
Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.
Identifiants
pubmed: 30808170
doi: 10.1021/acs.joc.9b00022
pmc: PMC6454400
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
4486-4500Références
J Am Chem Soc. 2003 Apr 9;125(14):4362-7
pubmed: 12670260
Angew Chem Int Ed Engl. 2005 Jan 28;44(6):947-9
pubmed: 15630711
J Magn Reson. 2005 Jun;174(2):237-44
pubmed: 15862240
J Am Chem Soc. 2005 Aug 31;127(34):12090-7
pubmed: 16117550
Carbohydr Res. 2006 Nov 27;341(16):2714-6
pubmed: 17014831
Org Lett. 2007 May 10;9(10):1959-62
pubmed: 17432867
Angew Chem Int Ed Engl. 2009;48(11):1900-34
pubmed: 19173361
Chem Commun (Camb). 2009 Oct 21;(39):5841-3
pubmed: 19787115
Nat Chem. 2009 Nov;1(8):611-22
pubmed: 20161474
Nat Chem. 2010 Jul;2(7):552-7
pubmed: 20571573
Org Lett. 2011 Jan 21;13(2):284-7
pubmed: 21158475
Org Lett. 2011 Mar 18;13(6):1544-7
pubmed: 21323371
Org Lett. 2011 Jun 3;13(11):2928-31
pubmed: 21563800
Chemistry. 2012 Jan 2;18(1):321-33
pubmed: 22140005
Carbohydr Res. 2012 Feb 1;348:6-13
pubmed: 22200482
J Am Chem Soc. 2012 May 2;134(17):7545-52
pubmed: 22475263
Org Lett. 2012 Nov 2;14(21):5468-71
pubmed: 23075145
Chem Sci. 2015 May 1;6(5):2687-2704
pubmed: 26078847
Chemistry. 2015 Sep 7;21(37):12920-6
pubmed: 26250358
Org Lett. 2015 Sep 4;17(17):4376-9
pubmed: 26308903
J Am Chem Soc. 2016 Mar 9;138(9):3002-11
pubmed: 26878147
J Org Chem. 2016 Jun 17;81(12):4988-5006
pubmed: 27224456
Chemistry. 2017 Dec 14;23(70):17637-17653
pubmed: 28741787