172039-03-1

Basic information

• Product Name: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate
• Synonyms: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate
• CAS NO: 172039-03-1
• Molecular Weight: 369.398
• Mol File: 172039-03-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate(172039-03-1)
• EPA Substance Registry System: (3aR,5R,6S,6aR)-5-(azidomethyl)tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate(172039-03-1)

Safety Data

• Hazardous Substances Data: 172039-03-1(Hazardous Substances Data)

Upstream product

• 4711-03-9 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 4119-18-0 2,2-dimethyl-6-(4-methylphenylsulfonyloxymethyl)-5-(4-methylphenylsulfonyloxymethyl)-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole 

Downstream Products

• 172039-05-3 1,2-di-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-D-xylofuranose 
• 1206797-39-8 (3aR,5R,6S,6aR)-5-(tert-butyloxycarbonylaminomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 172039-09-7 1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-trifluoromethyluracil 
• 172039-07-5 1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-iodouracil 
• 172039-08-6 1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-fluorouracil 
• 172039-06-4 1-(2-O-acetyl-5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)thymine 
• 172039-12-2 1-(5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-fluorouracil 

Relevant articles and documents

Clickable 4-Oxo-β-lactam-Based Selective Probing for Human Neutrophil Elastase Related Proteomes

Human neutrophil elastase (HNE) is a serine protease associated with several inflammatory processes such as chronic obstructive pulmonary disease (COPD). The precise involvement of HNE in COPD and other inflammatory disease mechanisms has yet to be clarified. Herein we report a copper-catalyzed alkyne–azide 1,3-dipolar cycloaddition (CuAAC, or ′click′ chemistry) approach based on the 4-oxo-β-lactam warhead that yielded potent HNE inhibitors containing a triazole moiety. The resulting structure–activity relationships set the basis to develop fluorescent and biotinylated activity-based probes as tools for molecular functional analysis. Attaching the tags to the 4-oxo-β-lactam scaffold did not affect HNE inhibitory activity, as revealed by the IC50values in the nanomolar range (56–118 nm) displayed by the probes. The nitrobenzoxadiazole (NBD)-based probe presented the best binding properties (ligand efficiency (LE)=0.31) combined with an excellent lipophilic ligand efficiency (LLE=4.7). Moreover, the probes showed adequate fluorescence properties, internalization in human neutrophils, and suitable detection of HNE in the presence of a large excess of cell lysate proteins. This allows the development of activity-based probes with promising applications in target validation and identification, as well as diagnostic tools.

Chemoselective reduction of azides catalyzed by molybdenum xanthate by using phenylsilane as the hydride source

A chemoselective, neutral, and efficient strategy for the reduction of azides to corresponding amines catalyzed by dioxobis(N,N,-diethyldithiocarbamato) molybdenum complex (1, MoO2[S2CNEt2]2) in the presence of phenylsilane is discovered. This chemoselective reduction strategy tolerates a variety of reducible functional groups.

Synthesis and reactions of 1-(5-azido-5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl) derivatives of 5-alkyl- and 5-halo-pyrimidines

Chemical syntheses of 1-(2-O-acetyl-5-azido--5-deoxy-3-O-p-toluenesulfonyl-β-D-xylofuranosyl)-5-iodo,- -5-fluoro-, and -5-trifluoromethyl-uracil nucleosides (11-13) as well as the thymine analogue 10 were performed from a sugar precursor and the correspon