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.

doi:10.1039/c8sc02788a

All Outputs (5)

d-Glucuronate and d-Glucuronate Glycal Acceptors for the Scalable Synthesis of d-GlcN-α-1,4-d-GlcA Disaccharides and Modular Assembly of Heparan Sulfate (2023)
Journal Article
Pongener, I., & Miller, G. J. (in press). d-Glucuronate and d-Glucuronate Glycal Acceptors for the Scalable Synthesis of d-GlcN-α-1,4-d-GlcA Disaccharides and Modular Assembly of Heparan Sulfate. Journal of Organic Chemistry, 88(15), 11130-11139. https://doi.org/10.1021/acs.joc.3c01108

Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. (2023)
Journal Article
Porter, J., Lima, M. A., Pongener, I., & Miller, G. (2023). Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. Carbohydrate Research, 524, Article 108759. https://doi.org/10.1016/j.carres.2023.108759

Sulfur containing glycosides offer an exciting prospect for inclusion within noncanonical glycan sequences, particularly as enabling probes for chemical glycobiology and for carbohydrate-based therapeutic development. In this context, we required acc... Read More about Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose..

Stereoselective beta-mannosylations and beta-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide (2021)
Journal Article
Pongener, I., Pepe, D. A., Ruddy, J. J., & McGarrigle, E. M. (2021). Stereoselective beta-mannosylations and beta-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide. Chemical Science, 12(29), 10070-10075. https://doi.org/10.1039/d1sc01300a

Stereoselective β-mannosylation is one of the most challenging problems in the synthesis of oligosaccharides. Herein, a highly selective synthesis of β-mannosides and β-rhamnosides from glycosyl hemi-acetals is reported, following a one-pot chlorinat... Read More about Stereoselective beta-mannosylations and beta-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide.

Synthesis of glycosyl chlorides using catalytic Appel conditions (2019)
Journal Article
Pongener, I., Nikitin, K., & McGarrigle, E. M. (in press). Synthesis of glycosyl chlorides using catalytic Appel conditions. Organic and Biomolecular Chemistry, 17(32), 7531-7535. https://doi.org/10.1039/c9ob01544b

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment... Read More about Synthesis of glycosyl chlorides using catalytic Appel conditions.

Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings (2018)
Journal Article
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

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