765884-92-2

Upstream product

• 222973-49-1 <(1R,4R,5S,6S)-4,5,6-tribenzyloxycyclohex-2-en-1-yl>amine 
• 222973-47-9 O-<(1S,4S,5R,6R)-4,5,6-tribenzyloxycyclohex-2-en-1-yl> trichloroacetimidate 
• 222973-48-0 α,α,α-trichloro-N-<(1R,4R,5S,6S)-4,5,6-tribenzyloxycyclohex-2-en-1-yl>acetamide 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 129745-62-6 (-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one 
• 129745-61-5 (+)-(1R,4R,5S,6S)-5-exo,6-endo-dihydroxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 129829-53-4 (+)-(1R,4R,5R,6R)-2,2-bis(benzyloxy)-5,6-exo-epoxy-7-oxabicyclo<2.2.1>heptane 
• 872976-90-4 (-)-(1R,2S,3S,4R)-4-phthalimidocyclohex-5-ene-1,2,3-triol 

Relevant academic research and scientific papers

(1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation

(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)3.

A synthesis of conduramine B and a 'condurithiol', useful molecules for studying the inhibition of β-xylosidases

Conduramine B and a 'condurithiol', namely (1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol and 1R,2S,3R,6R)-6-sulfanylcyclohex-4-ene-1,2,3-triol, have been prepared by the thermal rearrangement of an acetimidate and a dithiocarbonate, respectively. Both the amine and the thiol are putative inhibitors of β-xylosidases and, in order to mimic the natural substrate more closely, an N- and an S-pseudo-disaccharide have been prepared.