172822-67-2

Upstream product

• 172688-43-6 4-azido-4-deoxy-L-rhamnono-1,5-lactone 
• 172688-44-7 4-azido-4-deoxy-2,3-O-isopropylidene-L-rhamnono-1,5-lactone 
• 172688-45-8 4-azido-4-deoxy-2,3-O-isopropylidene-L-rhamnonoamide 
• 216483-78-2 4-azido-4-deoxy-α-L-rhamnopyranoside 
• 139285-80-6 methyl 6-deoxy-2,3-O-isopropylidene-4-O-(trifluoromethylsulfonyl)-α-L-talopyranoside 
• 18719-97-6 methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 24562-43-4 methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 2592-53-2 methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose 
• 172688-46-9 4-azido-4-deoxy-2,3-O-isopropylidene-L-rhamnononitrile 

Relevant academic research and scientific papers

Tetrazoles of manno- and rhamno- furanoses

The synthesis of [3.3.0] bicyclic tetrazoles derived from D-manno and D- rhamnofuranose staffing from D-mannose, and of L-rhamnofuranose starting from L-rhamnose is described. The key step in the formation of all three examples of this novel class of sugar mimics is an intramolecular [1,3]dipolar cycloaddition of azide and nitrile moieties.

Tetrazoles of manno- and rhamno-furanoses

The synthesis of tetrazoles derived from D-mannofuranose and both enantiomers of rhamnofuranose provides the first examples of tetrazole analogues of carbohydrates in the furanose form. The D-furanotetrazoles are potential mannosidase inhibitors whereas the L-rhamnotetrazole may interfere with the biosynthesis of cell walls of mycobacteria and provide a strategy for the treatment of tuberculosis and leprosy.