1366422-72-1

Basic information

• Product Name: (2R,3R,4R)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tertbutyldimethylsilyloxy)methyl)azetidine
• Synonyms: (2R,3R,4R)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tertbutyldimethylsilyloxy)methyl)azetidine
• CAS NO: 1366422-72-1
• Molecular Weight: 427.659
• Mol File: 1366422-72-1.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tertbutyldimethylsilyloxy)methyl)azetidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tertbutyldimethylsilyloxy)methyl)azetidine(1366422-72-1)
• EPA Substance Registry System: (2R,3R,4R)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tertbutyldimethylsilyloxy)methyl)azetidine(1366422-72-1)

Safety Data

• Hazardous Substances Data: 1366422-72-1(Hazardous Substances Data)

Upstream product

• 1366423-10-0 C₂₆H₃₁NO₆S 
• 1366423-12-2 C₃₂H₄₃NO₅SSi 
• 1366422-64-1 (S)-4-((2R,3S)-3-(benzyloxymethyl)oxiran-2-yl)-2,2-dimethyl-1,3-dioxolane 
• 1366422-66-3 (S)-4-((1R,2R)-2-azido-1,3-bis(benzyloxy)propyl)-2,2-dimethyl-1,3-dioxolane 
• 1366422-68-5 N-((1R,2R)-1,3-bis(benzyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-4-methylbenzenesulfonamide 
• 1366422-70-9 N-((2R,3R,4S)-1,3-bis(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-hydroxypentan-2-yl)-4-methylbenzenesulfonamide 
• 1366423-06-4 C₈H₁₄O₄ 
• 1366423-08-6 C₁₅H₂₁N₃O₄ 
• 1366423-14-4 C₂₂H₂₉NO₄ 
• 106757-57-7 (R,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)prop-2-en-1-ol 
• 36326-38-2 ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 

Downstream Products

• 1366423-16-6 ((2R,3S,4R)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol 
• 1366422-74-3 ((2R,3S,4R)-3-(benzyloxy)-4-(benzyloxymethyl)-1-butylazetidin-2-yl)methanol 

Relevant articles and documents

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.