283170-19-4

Upstream product

• 108-98-5 thiophenol 
• 179913-39-4 1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose 

Downstream Products

• 264626-95-1 phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-... 
• 264626-96-2 4-azido-6-(4-azido-6-{4-azido-6-[4-azido-6-(4-azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-ol 
• 264626-97-3 C₃₇H₅₃N₁₅O₁₀S 
• 264626-92-8 phenyl [[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside 
• 264626-93-9 phenyl [[(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside 
• 284025-40-7 Trifluoro-methanesulfonic acid (2S,3R,4S,6S)-4-azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 284025-41-8 Benzoic acid (2S,3S,4S,6S)-4-azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 264626-90-6 ((2S,3S,4S)-4-Azido-6-benzenesulfinyl-2-methyl-tetrahydro-pyran-3-yloxy)-trimethyl-silane 
• 264626-89-3 (2S,3S,4S,6S)-4-Azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 283170-20-7 (2S,3R,4S,6S)-4-Azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

General method for the synthesis of α- Or β-deoxyaminoglycosides bearing basic nitrogen

The introduction of glycosides bearing basic nitrogen is challenging using conventional Lewis acid-promoted pathways owing to competitive coordination of the amine to the Lewis acid promoter. Additionally, because many aminoglycosides lack a C2 substituent, diastereomeric mixtures of O-glycosides are often produced. Herein, we present a method for the synthesis of α- or β- 2,3,6-trideoxy-3-amino- and 2,4,6-trideoxy-4-amino O-glycosides from a common precursor. Our strategy proceeds by the reductive lithiation of thiophenyl glycoside donors and trapping of the resulting anomeric anions with 2-methyltetrahydropyranyl peroxides. We apply this strategy to the synthesis of α- and β-forosamine, pyrrolosamine, acosamine, and ristosamine derivatives using primary and secondary peroxides as electrophiles. α-Linked products are obtained in 60-96% yield and with >50:1 selectivity. β-Linked products are obtained in 45-94% yield and with 1.7->50:1 stereoselectivity. Contrary to donors bearing an equatorial amine substituent, donors bearing an axial amine substituent favored β-products at low temperatures. This work establishes a general strategy to synthesize O-glycosides bearing a basic nitrogen.

A practical method for the stereoselective generation of β-2-deoxy glycosyl phosphates

(Equation Presented) β-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize β-2-deoxy sugar phosphates that starts from α-glycosyl chlorides. Our approach reliably prov

Design of an oligosaccharide scaffold that binds in the minor groove of DNA

Many biological recognition events involve extensive interactions between macromolecules. Strategies to design compounds that mimic large peptides or other elements of secondary structure could be useful for blocking interactions between large surfaces. I