221276-73-9

Upstream product

• 78260-12-5 (2S,3R)-3-ethenyloxirane-2-methanol 
• 221216-43-9 (R)-4-((2S,3R)-3-((benzyloxy)methyl)oxiran-2-yl)-2,2-dimethyl-1,3-dioxolane 
• 120132-30-1 (2S,3R)-2-Benzyloxymethyl-3-vinyl-oxirane 
• 922-65-6 divinylcarbinol 

Downstream Products

• 221216-48-4 (R)-4-((1S,2S)-2-azido-1,3-bis(benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolane 
• 1366422-94-7 ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-butylazetidin-2-yl)methanol 
• 1366423-20-2 ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol 
• 1366422-92-5 (2S,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tert-butyldimethylsilyloxy)methyl)azetidine 
• 221216-64-4 N-((2S,3S,4R)-1,3-bis(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-hydroxypentan-2-yl)-4-methylbenzenesulfonamide 
• 221216-70-2 (2S,3S,4S)-3-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-azetidine 
• 221216-53-1 N-((1S,2S)-1,3-bis(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-4-methylbenzenesulfonamide 
• 221216-58-6 N-((1S,2S,3R)-2-Benzyloxy-1-benzyloxymethyl-3,4-dihydroxy-butyl)-4-methyl-benzenesulfonamide 
• 221216-35-9 [(2S,3R,4S)-3-Benzyloxy-4-benzyloxymethyl-1-(toluene-4-sulfonyl)-azetidin-2-yl]-methanol 
• 688741-90-4 (2R,3S,4S)-3-Benzyloxy-4-benzyloxymethyl-1-(toluene-4-sulfonyl)-azetidine-2-carbaldehyde 
• 221217-34-1 (2S,3R,4S)-2-Hydroxymethyl-4-((11S,12S)-11-hydroxy-12-methyl-tetradecyl)-1-(toluene-4-sulfonyl)-azetidin-3-ol 
• 135574-62-8 (15S,16S)-Penaresidin A 

Relevant academic research and scientific papers

Novel enantioselective synthesis of penaresidin A and Allo-penaresidin A via the construction of a highly functionalized azetidine

A new and highly enantioselective synthesis of penaresidin A has been achieved via the construction of a highly functionalized azetidine with the requisite stereogenic centers, which can also be regarded as an advanced intermediate for the synthesis of penaresidin B and penazetidine A.

MultiLigand Agent for Drug Delivery

Described herein is a compound having the structure of formula I, II, or III, wherein R comprises a double stranded RNA molecule, and L1, L2, and L3 independently for each occurrence comprise a ligand selected from the group consisting of a carbohydrate, a cholesteryl, or a peptide; a pharmaceutically accepted salt or pharmaceutical composition thereof; and a method of making the compound.

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.