857892-48-9

Upstream product

• 98-88-4 benzoyl chloride 
• 14218-11-2 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 857892-43-4 triphenylmethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 616238-31-4 triphenylmethyl 1-thio-α-D-mannopyranoside 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 857892-44-5 triphenylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Stereoselective Epimerizations of Glycosyl Thiols

Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

2-Haloethyl 1-thioglycosides as new tools in glycoside syntheses. Part 1: Preparation, characteristics, general reactions

2-Haloethyl 1-thioglycosides are excellent leaving groups when the 2-haloethyl function is activated with silver salts or Lewis acids. These thioglycosides can be synthesized on the original Cerny route or for better compatibility with the needs of a more complex glycoside synthesis, in stepwise procedures via 2-(2-tetrahydropyran-2-yloxy)ethyl glycosides or trityl 1-thioglycosides. The initial step in glycosidation reaction presumably proceeds via a thiiranium ion, which is responsible for their increased reactivity compared with normal thioethers as leaving groups in glycoside syntheses. Basic features of this new system with respect to reactivity and selectivity in disaccharide syntheses are described.