166516-67-2

Basic information

• Product Name: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside
• Synonyms: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside
• CAS NO: 166516-67-2
• Molecular Formula: C₁₂H₁₅N₃O₄S
• Molecular Weight: 297.3302
• Mol File: 166516-67-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(166516-67-2)
• EPA Substance Registry System: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(166516-67-2)

Safety Data

• Hazardous Substances Data: 166516-67-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is used as a labeling probe for glycoproteins to enable the study of their structure and function in biological systems.
Used in Click Chemistry:
It is used as a component in click chemistry for attaching fluorescent or other tags to glycoproteins, which aids in the visualization and analysis of their behavior within biological contexts.
Used as a Substrate for Enzymes:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is used as a substrate for enzymes involved in glycosylation, which is a crucial process in the biosynthesis of glycoproteins and other glycoconjugates.
Used in Laboratory Settings:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is primarily used in laboratory settings for the study of glycoprotein structure and function, contributing to the understanding of their roles in various biological processes and potential applications in medicine and biotechnology.

Upstream product

• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-98-5 thiophenol 
• 405290-56-4 phenyl 4,6-di-O-acetyl-3-O-benzoyl-1-thio-β-D-mannopyranoside 
• 246875-59-2 phenyl 4,6-di-O-acetyl-2,3-O-isopropylidne-1-thio-β-D-mannopyranoside 
• 246875-61-6 phenyl 4,6-di-O-acetyl-1-thio-β-D-mannopyranoside 
• 151662-55-4 phenyl 2,3:4,6-bis-O-isopropylidene-1-thio-β-D-mannopyranoside 
• 405290-57-5 phenyl 4,6-di-O-acetyl-2-azido-3-O-benzoyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 277756-84-0 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Stereoselectivity of Conformationally Restricted Glucosazide Donors

Glycosylations of 4,6-tethered glucosazide donors with a panel of model acceptors revealed the effect of acceptor nucleophilicity on the stereoselectivity of these donors. The differences in reactivity among the donors were evaluated in competitive glycosylation reactions, and their relative reactivities were found to be reflected in the stereoselectivity in glycosylations with a set of fluorinated alcohols as well as carbohydrate acceptors. We found that the 2-azido-2-deoxy moiety is more β-directing than its C-2-O-benzyl counterpart, as a consequence of increased destabilization of anomeric charge development by the electron-withdrawing azide. Additional disarming groups further decreased the α-selectivity of the studied donors, whereas substitution of the 4,6-benzylidene acetal with a 4,6-di-tert-butyl silylidene led to a slight increase in α-selectivity. The C-2-dinitropyridone group was also explored as an alternative for the nonparticipating azide group, but this protecting group significantly increased β-selectivity. All studied donors exhibited the same acceptor-dependent selectivity trend, and good α-selectivity could be obtained with the weakest acceptors and most reactive donors.

An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate

Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but the hydrogen sulfate

Agonistic and antagonistic properties of a Rhizobium sin-1 lipid A modified by an ether-linked lipid

LPS from Rhizobium sin-1 (R. sin-1) can antagonize the production of tumor necrosis factor alpha (TNF-α) by E. coli LPS in human monocytic cells. Therefore these compounds provide interesting leads for the development of therapeutics for the prevention or

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

The practical synthesis of carbohydrate-based NHC-Rh complexes bearing C1 or C3 sterically differentiated positions, accessed by glycosylation or SNAr strategies, is reported. These catalysts exhibit pseudo-enantiomeric behaviour in the hydrosilylation of acetophenone. We show that steric bulk at C1 gives preference for (S)-phenyl-1-ethanol, while bulk at C3 leads to the (R)-enantiomer. These results represent the first example of pseudo-enantiomeric carbohydrate-based NHC ligands leading to enantiotopic discrimination.

Design, synthesis and evaluation of cytotoxic properties of bisamino glucosylated antitumor ether lipids against cancer cells and cancer stem cells

Glycosylated antitumor ether lipids (GAELs) are a class of amphiphilic antitumor agents that kill cancer cells by a non-apoptotic pathway. Previous studies have shown that 2-amino-2-deoxy-d-gluco-based GAELs such as α-GLN and β-GLN show greatly improved antitumor activity against epithelial cancer cells and stem cells. To further optimize the bioactivity, we prepared a series of diamino-d-gluco-based GAELs and their analogs, and screened them against a panel of human epithelial cancer cell lines and cancer stem cells. Most of the new GAEL analogs are more potent than chlorambucil, cisplatin and salinomycin. The most potent bisamine-based GAEL analogs 1, 2, 4 and 8 showed 2- to 3-fold enhanced cytotoxicity against various cancer cell lines when compared to β-GLN, indicating that the addition of a second amino group enhances the cytotoxic effect. The effect of the most active dicationic GAELs 1 and 4 on cancer stem cells isolated from breast (BT-474) and prostate (DU-145) cell lines revealed that the two GAELs inhibited the formation of tumor spheres and resulted in >95% loss of viability of the cancer stem cells at 5 μM. Activity of GAEL 1 against BT-474 cancer stem cells is superior to that of salinomycin.

DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS

Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable

Oligo-Aminosaccharide compound

An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.

Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives

A library of forty modified aminoglycosides was prepared in which the configuration and regiochemistry of two or three rings was widely varied. The library was based around three core ring systems: the 2-deoxystreptamine ring system found in the natural products, and both enantiomers of (1R*,2R*,4R*,5R*)-2,5-diamino-cyclohexane-1,4-diol and (1R*,3R*,4R*,6R*)-4,6-diaminocyclohexane-1,3-diol. In each case, the core was modified by glycosylation with one or two sugar rings. The absolute configuration of the sugar substituents (D or L), the configuration of the anomeric centres (α or β), and the regiochemical arrangement of the amine(s) were varied. The Royal Society of Chemistry 2005.

Large scale synthesis of 2-azidodeoxy glucosyl donors

Starting from readily available phenyl 1-thio-β-D-mannopyranoside, phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (9) was synthesized on multigram scale using inexpensive reagents.