437757-90-9

Upstream product

• 217456-63-8 (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran 
• 53269-95-7 benzyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 105539-37-5 (E)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-phenyl-D-gluco-hept-1-enitol 
• 216869-51-1 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(phenyl)methylidene-D-glucopyranose 
• 437758-24-2 (R)-phenylbromomethyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 437758-25-3 (S)-phenylbromomethyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 105539-37-5 (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran 

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.

A Ramberg-Backlund approach to exo-glycals

A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes.