213617-00-6

Upstream product

• 89361-52-4 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranose 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 

Downstream Products

• 213617-01-7 C₄₂H₄₆INO₄Si 
• 213617-02-8 (2R,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyrrole 1-oxide 
• 897048-83-8 (5S,6R,7S)-6,7-dibenzyloxy-5-benzyloxymethyl-4-azaspiro[2.4]heptane 
• 897048-82-7 2,3,5-tri-O-benzyl-4-O-methanesulfonyl-D-ribononitrile 

Relevant academic research and scientific papers

A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available d-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against β-hexosaminidase with an IC50 value of 0.2 μM.

Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitors

Polyhydroxy 4-azaspiro[2.4]heptane derivatives (spirocyclopropyl iminosugars) were prepared in four to six steps from readily available protected aldoses. The key step of the reaction sequence involves a titanium-mediated aminocyclopropanation of glyconon

Synthesis and reactions of chiral cyclic nitrones derived from D-ribose

A facile route to chiral cyclic nitrones derived from D-ribose is described. Their versatility as substrates for 1,3-dipolar cycloadditions and nucleophilic additions is demonstrated.