Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings

Bradshaw, G. A.; Colgan, A. C.; Allen, N. P.; Pongener, I.; Boland, M. B.; Ortin, Y.; McGarrigle, E. M.

Abstract

Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. It is proposed that in these glycosylations thiouracil, monothiophthalimide, and the previously reported catalyst, Schreiner's thiourea, do not operate via a double H-bonding mechanism but rather by Brønsted acid/base catalysis. In addition to the synthesis of 2-deoxyglycosides and glycoconjugates, we report the first organocatalytic synthesis of 1,1′-linked trehalose-type sugars.

Citation

Bradshaw, G. A., Colgan, A. C., Allen, N. P., Pongener, I., Boland, M. B., Ortin, Y., & McGarrigle, E. M. (in press). Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings. Chemical Science, 10(2), 508-514. https://doi.org/10.1039/c8sc02788a

• Journal Article Type: Article
• Acceptance Date: Oct 22, 2018
• Online Publication Date: Oct 15, 2018
• Deposit Date: Jun 16, 2023
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Electronic ISSN: 2041-6539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 10
• Issue: 2
• Pages: 508-514
• DOI: https://doi.org/10.1039/c8sc02788a
• Keywords: General Chemistry
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : A. C. Colgan (ORCID); : I. Pongener (ORCID); : E. M. McGarrigle (ORCID); : Single-blind; : Received 25 June 2018; Accepted 15 October 2018; Advance Article published 22 October 2018; Version of Record published 2 January 2019