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

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

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

Downstream Products

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

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.

Reversible lysine modification on proteins by using functionalized boronic acids

Iminoboronates have been utilized to successfully install azide and alkyne bioorthogonal functions on proteins, which may then be further reacted with their bioorthogonal counterparts. These constructs were also used to add polyethylene glycol (PEG) to insulin, a modification which has been shown to be reversible in the presence of fructose. Finally, iminoboronates were used to assemble a folic acid/paclitaxel small-molecule/drug conjugate in situ with an IC50 value of 20.7 nM against NCI-H460 cancer cells and negligible cytotoxicity against the CRL-1502 noncancer cells. Easy installation: The use of iminoboronates is a successful strategy to install diverse functions on proteins (see picture; GSH=glutathione, PEG=polyethylene glycol) and to assemble a folic acid/paclitaxel small-molecule/drug conjugate in situ.

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 of 5-amino-5-deoxypentonolactams

5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropy-lidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5

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