852045-24-0

Upstream product

• 852045-20-6 (1s,2R,3S,4r,5R,6S)-2,3,4,5,6-pentakis(benzyloxy)cyclohexanamine 
• 111-64-8 n-octanoic acid chloride 
• 868550-22-5 (1S,2S,3R,4R,5S,6R)-1-azido-2,3,4,5,6-pentakis-benzyloxycyclohexane 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 526-87-4 (+/-)-Conduritol B 
• 6090-95-5 conduritol β-epoxide 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide

A systematic approach to the regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols arising from tetra-O-benzylconduritol B epoxide (9) and its aziridine analogue 22, respectively, is described. In all cases, the synthetic methodologies rely on the regio- and stereocontrolled azidolysis of the starting precursors to give the corresponding trans regioadducts. Subsequent functional group manipulation under strict configurational control affords the isomeric cis adducts. Chemoselective functionalization of the diamine moiety in 1,2-diaminoinositol derivatives can be achieved by the proper design of the reaction sequence and choice of reagents. The described protocols allow efficient access to each of the eight possible configurations of the 1,2-diamino and 1,2-amino alcohol moieties from chemical modifications of the epoxide moiety on the common precursor 9.

New aminocyclitols as modulators of glucosylceramide metabolism

A series of 13 aminocyclitol derivatives belonging to two different families is described. Their configuration is governed by the regio- and stereocontrolled epoxide opening of a suitably protected conduritol-B epoxide. Studies on several glycosyl processing enzymes indicate that some of them are good inhibitors of glucosylceramide hydrolase. A rationale to account for preliminary structure-activity relationships is provided. The Royal Society of Chemistry 2005.