652990-16-4

Upstream product

• 54535-06-7 bis(o-phenylene)glycol ditosylate 
• 74761-34-5 1’,2,3,3’,4,4’-hexa-O-benzylsucrose 
• 652990-14-2 1′,2,2′,3,3′,4,4′-hexa-O-benzyl-6,6′-dideoxy-6,6′-di-chlorosucrose 
• 392699-44-4 6-O-acetyl-1,3,4-tri-O-benzyl-β-D-fructofuranosyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Macrocyclic receptors containing sucrose skeleton

Crown ether analogues with incorporated sucrose unit were prepared by reaction of 1′,2,3,3′,4,4′-hexa-O-benzylsucrose with polyethylene ditosylates in up to 52% yield. Stability constants of their complexes with Li+, Na+, K+, NH 4+ were determined by the NMR titration method. The macrocycles were also tested as catalysts in the enantioselective Michael reaction, but with little success (ee up to only 22%). The macrocycle containing nitrogen in the ring was also prepared in good yield. All prepared macrocycles were easily converted into the free sucrose crowns (H2/Pd/C) without destroying the (very labile) glycosidic bond. The crystal structure of the selected receptor was determined.

Synthesis of Macrocyclic Derivatives Containing a Sucrose Unit

An efficient synthesis of 1′,2,3,3′4,4′-hexa-O- benzylsucrose (48% from sucrose) is presented. This diol was used for the preparation of crown ether-type analogs of various size macrocyclic rings with incorporated sucrose units.