216871-80-6

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 437758-21-9 benzyl S,S-dioxo-1-thio-β-D-glucopyranoside 
• 100-53-8 phenylmethanethiol 
• 83-87-4 D-glucose pentaacetate 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 216871-75-9 benzyl S,S-dioxo-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 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 
• 216871-90-8 (2R,3S,4S,5R)-2-Hydroxymethyl-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

A new route to exo-glycals using the Ramberg-Baecklund rearrangement

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Baecklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

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.