289698-50-6

Upstream product

• 3173-56-6 benzyl isothiocyanate 
• 289698-46-0 (1S,2S,3R,4R)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylidenecyclopentane-2,3,4-triol 
• 289698-47-1 (1S,2S,3R,4R,5S)-2-O-(benzylcarbamoyl)-1-bromo-3,4-O-isopropylidene-5-methylcyclopentane-2,3,4-triol 
• 289698-45-9 (1S,2S,3S,4R)-1-bromo-3,4-O-isopropylidene-5-methylidenecyclopentane-2,3,4-triol 
• 229962-61-2 (1aS,1bS,4aS,5aS)-tetrahydro-3,3-dimethyl-5H-oxireno[3,4]cyclopenta[1,2-d][1,3]dioxol-5-one 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 286851-33-0 (3aR,3bR,6aR,7R,7aR)-6-benzylhexahydro-2,2,7-trimethyl-5H-1,3-dioxolo[4,5:3,4]cyclopent[1,2-d]oxazol-5-one 

Relevant academic research and scientific papers

Aminocyclopentitol inhibitors of α-L-fucosidases

Aminocyclopentitol analogs of α-L-fucose were synthesized stercoselectively from D-ribose. Alkyl substituents were attached at the NH2 group to mimic the glycosidic leaving group. The resulting (alkylamino)cyclopentitols inhibited α-L-fucosidases selectively with inhibition constants in the range of Ki = 10-7 M. Comparisons with stereoisomers and acyclic analogs showed that this inhibition only occurs with N-alkyl substitution and proper configuration at the cyclopentane, as expected for transition-state-analog-type inhibition. These observations were supported by molecular-modeling comparisons between inhibitor and transition state.

Stereoselective synthesis of an aminocyclopentitol analog of α-L-fucose via an allylic bromohydrin

Selective opening of allylic epoxide 4 with lithium bromide in acetic acid provides an allylic bromohydrin (5). Chemo- and stereoselective hydrogenation of the corresponding benzyl carbamate 6 and intramolecular cyclization gives, after deprotection, (1R, 2R, 3R, 4R, 5R) 4-amino-5-methyl- cyclopentane-1,2,3-triol 3, an analog of α-L-fucose. This synthetic sequence provides one of the few stereoselective approaches to alpha-configurated aminocyclopentitols.