359714-89-9

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73111-58-7 2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose 
• 107-11-9 1-amino-2-propene 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 

Downstream Products

• 1366422-98-1 (5R,6S,7S)-tert-butyl 5,6,7-tris(benzyloxy)-5,6,7,8-tetrahydroazocine-1(2H)-carboxylate 
• 1366422-46-9 (3R,4R,5R,6R,7S)-5,6,7-tris(benzyloxy)-1-tosylazocane-3,4-diol 
• 1366422-48-1 (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-tosylazocane 
• 1366422-50-5 (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)azocane 
• 1366422-52-7 (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-butylazocane 
• 1366423-02-0 (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane 
• 1366422-96-9 tert-butyl N-allyl-((2S,3S,4R)-2,3,4-tris(benzyloxy)hex-5-en-1-yl)carbamate 
• 1366422-33-4 N-allyl-4-methyl-N-((2S,3S,4R)-2,3,4-tris(benzyloxy)hex-5-enyl)benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases

Eight- and four-membered analogues of N-butyldeoxynojirimycin (NB-DNJ), a reversible male contraceptive in mice, were prepared and tested. A chiral pool approach was used for the synthesis of the target compounds. Key steps for the synthesis of the eight-membered analogues involve ring-closing metathesis and Sharpless asymmetric dihydroxylation and for the four-membered analogues Sharpless epoxidation, epoxide ring-opening (azide), and Mitsunobu reaction to form the four-membered ring. (3S,4R,5S,6R,7R)-1-Nonylazocane-3,4,5,6,7-pentaol (6) was moderately active against rat-derived ceramide-specific glucosyltransferase, and four of the other eight-membered analogues were weakly active against rat-derived β-glucosidase 2. Among the four-membered analogues, ((2R,3S,4S)-3-hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (25) displayed selective inhibitory activity against mouse-derived ceramide-specific glucosyltransferase and was about half as potent as NB-DNJ against the rat-derived enzyme. ((2S,4S)-3-Hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (27) was found to be a selective inhibitor of β-glucosidase 2, with potency similar to NB-DNJ. Additional glycosidase assays were performed to identify potential other therapeutic applications. The eight-membered iminosugars exhibited specificity for almond-derived β-glucosidase, and the 1-nonylazetidine 25 inhibited α-glucosidase (Saccharomyces cerevisiae) with an IC50 of 600 nM and β-glucosidase (almond) with an IC50 of 20 μM. Only N-nonyl derivatives were active, emphasizing the importance of a long lipophilic side chain for inhibitory activity of the analogues studied.