216871-90-8

Upstream product

• 216871-75-9 benzyl S,S-dioxo-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 216871-80-6 benzyl S,S-dioxo-1-thio-2,3,4,6-tetra-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 437758-21-9 benzyl S,S-dioxo-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 216871-85-1 (2R,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran 

Relevant academic research and scientific papers

Synthetic applications of Ramberg-Backlund derived exo-glycals

Synthetic applications of the title glycals, prepared from S-glycoside dioxides using the Meyers' variant of the Ramberg-Backlund rearrangement are described. These include a formal total synthesis of a novel β-glycosidase inhibitor, and an efficient route to spirocyclic glucose derivatives. In addition, silyl methodology has been developed which allows unprotected exo- glycals to be synthesised.