111085-83-7

Upstream product

• 111085-79-1 1-(1,3,4,6-tetra-O-benzyl-D-fructofuranosyl)-2-propene 
• 100-39-0 benzyl bromide 
• 429675-56-9 (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane 
• 111085-82-6 (2R,3R,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-iodomethyl-1,7-dioxa-spiro[4.4]nonane 
• 111085-79-1 1-(1,3,4,6-tetra-O-benzyl-α-D-fructofuranosyl)-2-propene 
• 13403-14-0 methyl D-fructofuranoside 

Downstream Products

• 111085-88-2 (1-O-(tert-butyldimethylsilyl)-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)methyl benzoate 
• 111085-92-8 1-(1-O-(tert-butyldimethylsilyl)-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)-1-propene 
• 111085-85-9 1-(1-O-acetyl-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)-1-propene 
• 111085-93-9 1-(1-O-(tert-butyldimethylsilyl)-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)methanol 
• 111085-86-0 1-(1-O-acetyl-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)methanol 
• 111085-87-1 (3,4,6-tri-O-benzyl-α-D-fructofuranosyl)methanol 
• 111085-89-3 (1-O-benzoyl-3,4,6-tri-O-benzyl-β-D-fructofuranosyl)methanol 
• 487061-57-4 (2S,3R,3aS,5R,6R,6aS)-3a-Allyl-2-azidomethyl-6-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]furan-3-ol 
• 429675-58-1 (R)-1-((2S,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-prop-2-en-1-ol 
• 429675-61-6 (2R,3R,3aS,5R,6R,6aS)-3a-Allyl-6-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]furan-3-ol 
• 429675-57-0 (2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 111085-91-7 1-(1-O-(tert-butyldimethylsilyl)-3,4,6-tri-O-benzyl-α-D-fructofuranosyl)-2-propene 

Relevant academic research and scientific papers

Polycyclic scaffolds from fructose

Iodocyclisation of polybenzylated allyl α-C-fructofuranoside 1 afforded the bicyclic iodoether 2 through debenzylation at C-1; treatment of 2 with zinc and acetic acid restored the allylic group with concomitant deprotection of the hydroxyl group at C-1, which was oxidised to the corresponding aldehyde 4. Reaction of 4 with vinylmagnesium bromide afforded diene 5, whose double bonds were reacted regioselectively in order to obtain, upon iodocyclisation under different experimental conditions, bicycles 6 or 7, or tricycle 8.

Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds

The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments1 of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics.

Synthesis and conformational analysis of fructose-derived scaffolds: Molecular diversity from a single molecule

Bi- and tricyclic compounds were synthesized starting from fructose. The different hydroxyl groups present in fructose were exploited in the formation of a number of conformationally constrained sugar-based scaffolds, including azido acids. Introduction o