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

Synthesis of 4-thio-d-glucopyranose and interconversion to 4-thio-d-glucofuranose. (2023)
Journal Article

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

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

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

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.