Synthesis of glycosyl sulfoximines by a highly chemo- and stereoselective NH- and O-transfer to thioglycosides-Reference-Cited by-同舟云学术

Synthesis of glycosyl sulfoximines by a highly chemo- and stereoselective NH- and O-transfer to thioglycosides

Published:2020 Issue:20 Volume:18 Page:3893-3897
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Tota Arianna¹²³⁴,Carlucci Claudia¹²³⁴,Pisano Luisa⁵⁶⁷⁴,Cutolo Giuliano⁸⁹¹⁰,Clarkson Guy J.¹¹¹²¹³¹⁴^ORCID,Romanazzi Giuseppe¹⁵³⁴,Degennaro Leonardo¹²³⁴,Bull James A.¹¹¹⁶¹⁷¹⁸¹⁴^ORCID,Rollin Patrick¹⁹²⁰²¹²²^ORCID,Luisi Renzo¹²³⁴^ORCID

Affiliation:

1. Department of Pharmacy - Drug Sciences

2. University of Bari “A. Moro” Via E. Orabona 4

3. Bari 70125

4. Italy

5. Department of Chemistry and Pharmacy

6. University of Sassari

7. Sassari

8. PrattLab – University of Southern California

9. TRF 100 Los Angeles

10. USA

11. Department of Chemistry

12. University of Warwick

13. Coventry CV4 7AL

14. UK

15. DICATECh

16. Molecular Sciences Research Hub

17. Imperial College London

18. White City Campus

19. Université d'Orléans et CNRS

20. ICOA

21. F-45067 Orléans

22. France

Abstract

The first highly stereoselective sulfoximine formation directly from sulfides is achieved in the preparation of unprecedented glycosyl sulfoximines. X-ray analysis and a computational model establish the configuration at sulfur.

Funder

Universita degli Studi di Bari Aldo Moro

Royal Society of Chemistry

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB00647E

Reference35 articles.

1. S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

2. Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications